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Generation and α-hydroxyalkylation of a novel 3-piperidinol N-α-carbanion intermediate

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Abstract

The (S)-sulfide 6 has been synthesized as a synthetic equivalent of novel 3-piperidinol N-α-carbanion B via deprotonation and lithium naphthanelide (LN)-mediated reductive lithiation. The reaction of the 3-piperidinol N-α-carbanion intermediate B with carbonyl compounds gave, besides some reduced product 2a, the desired α-hydroxyalkylation products 12–17 with excellent 2,3-diastereoselectivity. The reductive α-hydroxyalkylation with unsymmetric carbonyl compounds led to only 50:50 to 77:23 diastereoselectivities at the C-1′ carbinol center.

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Authors and Affiliations

  1. Department of Chemistry and Key Laboratory for Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China

    Xiao Zheng, Guo Chen, YuanPing Ruan & PeiQiang Huang

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  1. Xiao Zheng
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  2. Guo Chen
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  3. YuanPing Ruan
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  4. PeiQiang Huang
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Correspondence to Xiao Zheng or YuanPing Ruan.

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Supported by the National Natural Science Foundation of China (Grant No. 20832005).

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Zheng, X., Chen, G., Ruan, Y. et al. Generation and α-hydroxyalkylation of a novel 3-piperidinol N-α-carbanion intermediate. Sci. China Ser. B-Chem. 52, 1631–1638 (2009). https://doi.org/10.1007/s11426-009-0229-2

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