Abstract
Transition metal-catalyzed cycloadditions of cyclopropanes have been well developed over the past several decades, leading to numerous new types of cycloadditions which are complementary to the traditional cycloadditions for the synthesis of carbocycles. Cycloadditions of vinylcyclopropanes (VCPs) and methylenecyclopropanes (MCPs) constitute two main aspects of this field. VCPs can act either as five-carbon synthons or three-carbon synthons, depending on whether the vinyl substituent is acting as an additional two-carbon synthon or not. As five-carbon synthons, VCPs are involved in [5+1], [5+2], [5+2+1], and [5+1+2+1] cycloadditions. As three-carbon synthons, VCPs are mainly involved in [3+2] and [3+2+1] cycloadditions. MCPs mostly act as three-carbon synthons and can have [3+2] cycloadditions with different π systems. Other types of cycloadditions involving MCPs are also reviewed, such as [3+1], [3+2+2], and [4+3+2] cycloadditions. Cycloadditions of some other unusual cyclopropane derivatives are also introduced briefly. The cycloadditions of VCPs and MCPs have found applications in total synthesis and some representative molecules are tabulated as selected examples.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
References
Rubin M, Rubina M, Gevorgyan V (2007) Chem Rev 107:3117
Ben-Shoshan R, Sarel S (1969) Chem Commun 883
Victor R, Ben-Shoshan R, Sarel S (1970) Tetrahedron Lett 49:4253
Sarel S (1978) Acc Chem Res 11:204
Aumann R (1974) J Am Chem Soc 96:2631
Schulze MM, Gockel U (1996) Tetrahedron Lett 37:357
Schulze MM, Gockel U (1996) J Organomet Chem 525:155
Taber DF, Kanai K, Jing Q, Bui G (2000) J Am Chem Soc 122:6807
Taber DF, Joshi PV, Kanai K (2004) J Org Chem 69:2268
Kurahashi T, de Meijere A (2005) Synlett 2619
Jiang GJ, Fu XF, Li Q, Yu ZX (2012) Org Lett 14:692
Iwasuwa N, Owada Y, Matsuo T (1995) Chem Lett 2:115
Owada Y, Matsuo T, Iwasuwa N (1997) Tetrahedron 53:11069
Murakami M, Itami K, Ubukata M, Tsuji I, Ito Y (1998) J Org Chem 63:4
Shu D, Li X, Zhang M, Robichaux PJ, Tang WP (2011) Angew Chem Int Ed 50:1346
Shu D, Li X, Zhang M, Robichaux PJ, Guzei IA, Tang WP (2012) J Org Chem 77:6463
Wender PA, Takahashi H, Witulski B (1995) J Am Chem Soc 117:4720
Wender PA, Husfeld CO, Langkopf E, Love JA (1998) J Am Chem Soc 120:1940
Wender PA, Husfeld CO, Langkopf E, Love JA, Plleuss N (1998) Tetrahedron 54:7203
Wender PA, Glorius F, Husfeld CO, Langkopf E, Love JA (1999) J Am Chem Soc 121:5348
Wender PA, Sperandio D (1998) J Org Chem 63:4164
Wender PA, Dykman AJ, Husfeld CO, Kadereit D, Love JA, Rieck H (1999) J Am Chem Soc 121:10442
Wender PA, Dykman AJ (1999) Org Lett 1:2089
Gilbertson SR, Hoge GS (1998) Tetrahedron Lett 39:2075
Wang B, Cao P, Zhang XM (2000) Tetrahedron Lett 41:8041
Lee SI, Park SY, Park JH, Jung IG, Choi SY, Chung YK, Lee BY (2006) J Org Chem 71:91
Saito A, Ono T, Hanzawa Y (2006) J Org Chem 71:6437
Wender PA, Williams TJ (2002) Angew Chem Int Ed 41:4550
Wender PA, Love JA, Williams TJ (2003) Synlett 1295
Gómez FJ, Kamber NE, Deschamps NM, Cole AP, Wender PA, Waymouth RM (2007) Organometallics 26:4541
Wender PA, Lesser AB, Sirois LE (2012) Angew Chem Int Ed 51:2736
Xu X, Liu P, Lesser A, Sirois LE, Wender PA, Houk KN (2012) J Am Chem Soc 134:11012
Wender PA, Haustedt LO, Lim J, Love JA, Willams TJ, Yoon JY (2006) J Am Chem Soc 128:6302
Shintani R, Nakatsu H, Takatsu K, Hayashi T (2009) Chem Eur J 15:8692
Inagaki F, Sugikubo K, Miyashita Y, Mukai C (2010) Angew Chem Int Ed 49:2206
Jiao L, Ye SY, Yu ZX (2008) J Am Chem Soc 130:7178
Wender PA, Rieck H, Fuji M (1998) J Am Chem Soc 120:10976
Wender PA, Dyckman AJ, Husfeld CO, Scanio MJC (2000) Org Lett 2:1609
Wender PA, Sirois LE, Stemmler RT, Williams TJ (2010) Org Lett 12:1604
Wender PA, Barzilay CM, Dyckman AJ (2001) J Am Chem Soc 123:179
Wegner HA, de Meijere A, Wender PA (2005) J Am Chem Soc 127:6530
Ashfeld BL, Miller KA, Smith AJ, Tran K, Martin SF (2005) Org Lett 7:1661
Ashfeld BL, Miller KA, Smith AJ, Tran K, Martin SF (2007) J Org Chem 72:9018
Wender PA, Stemmler RT, Sirois LE (2010) J Am Chem Soc 132:2532
Wender PA, Gamber GG, Scanio MJC (2001) Angew Chem Int Ed 40:3895
Yu ZX, Wender PA, Houk KN (2004) J Am Chem Soc 126:9154
Liu P, Sirois LE, Cheong PHY, Yu ZX, Hartung IV, Rieck H, Wender PA, Houk KN (2010) J Am Chem Soc 132:10127
Yu ZX, Cheong PHY, Liu P, Legault CY, Wender PA, Houk KN (2008) J Am Chem Soc 130:2378
Wang Y, Wang J, Su J, Huang F, Jiao L, Liang Y, Yang D, Zhang S, Wender PA, Yu ZX (2007) J Am Chem Soc 129:10060
Trost BM, Toste FD, Shen H (2000) J Am Chem Soc 122:2379
Trost BM, Shen HC (2000) Org Lett 2:2523
Trost BM, Shen HC (2001) Angew Chem Int Ed 40:1114
Trost BM, Shen HC, Schulz T, Koradin C, Schirok H (2003) Org Lett 5:4149
Trost BM, Toste FD (2001) Angew Chem Int Ed 40:2313
Trost BM, Shen HC, Horne DB, Toste FD, Steinmetz BG, Koradin C (2005) Chem Eur J 11:2577
Hong X, Trost NM, Houk KN (2013) J Am Chem Soc 135:6588
Zuo G, Louie J (2005) J Am Chem Soc 127:5798
Hong X, Liu P, Houk KN (2013) J Am Chem Soc 135:1456
Fürstner A, Majima K, Martin R, Krause H, Kattnig E, Goddard R, Lehmann CW (2008) J Am Chem Soc 130:1992
Wender PA, Gamber GG, Hubbard RD, Zhang L (2002) J Am Chem Soc 124:2876
Wender PA, Gamber GG, Hubbard RD, Pham SM, Zhang L (2005) J Am Chem Soc 127:2836
Huang F, Yao ZK, Wang Y, Wang YY, Zhang JL, Yu ZX (2010) Chem Asian J 5:1555
Liao W, Wang YY, Jiao L, Yu ZX (2014) unpublished result
Shimizu I, Ohashi Y, Tsuji J (1985) Tetrahedron Lett 26:3825
Dieskau AP, Holzwarth MS, Plietker B (2012) J Am Chem Soc 134:5048
Trost BM, Morris PJ (2011) Angew Chem Int Ed 50:6167
Trost BM, Morris PJ, Sprague SJ (2012) J Am Chem Soc 134:17823
Mei LY, Wei Y, Xu Q, Shi M (2012) Organometallics 31:7591
Mei LY, Wei Y, Xu Q, Shi M (2013) Organometallics 32:3544
Li Q, Jiang GJ, Jiao L, Yu ZX (2010) Org Lett 12:1332
Jiao L, Lin M, Yu ZX (2010) Chem Commun 46:1059
Jiao L, Lin M, Yu ZX (2011) J Am Chem Soc 133:447
Lin M, Kang GY, Guo YA, Yu ZX (2012) J Am Chem Soc 134:398
Jiao L, Lin M, Zhuo LG, Yu ZX (2010) Org Lett 12:2528
Lin M, Li F, Jiao L, Yu ZX (2011) J Am Chem Soc 133:1690
Kim SY, Lee SI, Choi SY, Chung YK (2008) Angew Chem Int Ed 47:4914
Trost BM (1986) Angew Chem Int Ed Engl 25:1
Binger P, Büch HM (1987) Top Curr Chem 135:77
Noyori R, Odagi T, Takaya H (1970) J Am Chem Soc 92:5780
Noyori R, Kumagai Y, Umeda I, Takaya H (1972) J Am Chem Soc 94:4018
Corlay H, Lewis RT, Motherwell WB, Shipman M (1995) Tetrahedron 51:3303
Yamago S, Nakamura E (1988) J Chem Soc Chem Commun 1112
Lautens M, Ren Y, Delanghe PHM (1994) J Am Chem Soc 116:8821
Lautens M, Klute W, Tam W (1996) Chem Rev 96:49
Nakamura I, Yamamoto Y (2002) Adv Synth Catal 344:111
Yu L, Guo R (2011) Org Prep Proced Int 43:209
Delgado A, Rodríguez JR, Castedo L, Mascareñas JL (2003) J Am Chem Soc 125:9282
López F, Delgado A, Rodríguez JR, Castedo L, Mascareñas JL (2004) J Am Chem Soc 126:10262
García-Fandiño R, Gulías M, Mascareñas JL, Cárdenas DJ (2012) Dalton Trans 41:9468
Trillo B, Gulías M, López F, Castedo L, Mascareñas JL (2006) Adv Synth Catal 348:2381
García-Fandiño R, Gulías M, Castedo L, Granja JR, Mascareñas JL, Cárdenas DJ (2008) Chem Eur J 14:272
Achard T, Lepronier A, Gimbert Y, Clavier H, Giordano L, Tenaglia A, Buono G (2011) Angew Chem Int Ed 50:3552
Yao B, Li Y, Liang ZJ, Zhang YH (2011) Org Lett 13:640
Kurahashi T, de Meijere A (2005) Angew Chem Int Ed 44:7881
Kurahashi T, Wu YT, Meindl K, Rühl S, de Meijere A (2005) Synlett 805
Kamikawa K, Shimizu Y, Takemoto S, Matsuzaka H (2006) Org Lett 8:4011
Mazumder S, Shang D, Negru DE, Baik MH, Evans PA (2012) J Am Chem Soc 134:20569
Ohashi M, Taniguchi T, Ogoshi S (2010) Organometallics 29:2386
Binger P, Schuchardt U (1980) Chem Ber 113:1063
Binger P, Brinkman A, McMeeking J (1977) Justus Liebigs Ann Chem 1065
Saito S, Masuda M, Komagawa S (2004) J Am Chem Soc 126:10540
Saito S, Komagawa S, Azumaya I, Masuda M (2007) J Org Chem 72:9114
Komagawa S, Takeuchi K, Sotome I, Azumaya I, Masu H, Yamasaki R, Saito S (2009) J Org Chem 74:3323
Komagawa S, Saito S (2006) Angew Chem Int Ed 45:2446
Yamasaki R, Terashima N, Sotome I, Komagawa S, Saito S (2010) J Org Chem 75:480
Maeda K, Saito S (2007) Tetrahedron Lett 48:3173
Saito S, Takeuchi K (2007) Tetrahedron Lett 48:595
Komagawa S, Wang C, Morokuma K, Saito S, Uchiyama M (2013) J Am Chem Soc 135:14508
Saito S, Maeda K, Yamasaki R, Kitamura T, Nakagawa M, Kato K, Azumaya I, Masu H (2010) Angew Chem Int Ed 49:1830
Yamasaki R, Ohashi M, Maeda K, Kitamura T, Nakagawa M, Kato K, Fujita T, Kamura R, Kinoshita K, Masu H, Azumaya I, Ogoshi S, Saito S (2013) Chem Eur J 19:3415
Evans PA, Inglesby PA (2008) J Am Chem Soc 130:12838
Saya L, Bhargava G, Navarro MA, Gulías M, López F, Fernández I, Castedo L, Mascareñas JL (2010) Angew Chem Int Ed 49:9886
Bhargava G, Trillo B, Araya M, López F, Castedo L, Mascareñas JL (2010) Chem Commun 46:270
Gulías M, Durán J, López F, Castedo L, Mascareñas JL (2007) J Am Chem Soc 129:11026
Ogoshi S, Nagata M, Kurosawa H (2006) J Am Chem Soc 128:5350
Tamaki T, Nagata M, Ohashi M, Ogoshi S (2009) Chem Eur J 15:10083
Tamaki T, Ohashi M, Ogoshi S (2011) Angew Chem Int Ed 50:12067
Liu L, Montgomery J (2006) J Am Chem Soc 128:5348
Liu L, Montgomery J (2007) Org Lett 9:3885
Koga Y, Narasaka K (1999) Chem Lett 7:705
Matsuda T, Tsuboi T, Murakami M (2007) J Am Chem Soc 129:12596
Lu BL, Wei Y, Shi M (2012) Organometallics 31:4601
Chen GQ, Shi M (2013) Chem Commun 49:698
Shaw MH, Melikhova EY, Kloer DP, Whittingham WG, Bower JF (2013) J Am Chem Soc 135:4992
Yao ZK, Li JJ, Yu ZX (2010) Org Lett 13:134
Zhang M, Tang WP (2012) Org Lett 14:3756
Wender PA, Fuji M, Husfeld CO, Love JA (1999) Org Lett 1:137
Wender PA, Zhang L (2000) Org Lett 2:2323
Ashfeld BL, Martin SF (2005) Org Lett 7:4535
Trost BM, Hu Y, Horne DB (2007) J Am Chem Soc 129:11781
Trost BM, Waser J, Meyer A (2007) J Am Chem Soc 129:14556
Jiao L, Yuan C, Yu ZX (2008) J Am Chem Soc 130:4421
Fan X, Tang MX, Zhuo LG, Tu YQ, Yu ZX (2009) Tetrahedron Lett 50:155
Fan X, Zhuo LG, Tu YQ, Yu ZX (2009) Tetrahedron 65:4709
Yuan C, Jiao L, Yu ZX (2010) Tetrahedron Lett 51:5674
Liang Y, Jiang X, Yu ZX (2011) Chem Commun 47:6659
Liang Y, Jiang X, Fu XF, Ye S, Wang T, Yuan J, Wang Y, Yu ZX (2012) Chem Asian J 7:593
Goldberg AFG, Stoltz BM (2011) Org Lett 13:4474
Evans PA, Inglesby PA, Kilbride K (2013) Org Lett 15:1798
Jiao L, Yu ZX (2013) J Org Chem 78:6842
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Gao, Y., Fu, XF., Yu, ZX. (2014). Transition Metal-Catalyzed Cycloadditions of Cyclopropanes for the Synthesis of Carbocycles: C–C Activation in Cyclopropanes. In: Dong, G. (eds) C-C Bond Activation. Topics in Current Chemistry, vol 346. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2014_527
Download citation
DOI: https://doi.org/10.1007/128_2014_527
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-55054-6
Online ISBN: 978-3-642-55055-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)