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Non-Salen Metal-Catalyzed Asymmetric Dihydroxylation and Asymmetric Aminohydroxylation of Alkenes. Practical Applications and Recent Advances

  • Steven J. MehrmanEmail author
  • Ahmed F. Abdel-Magid
  • Cynthia A. Maryanoff
  • Bart P. Medaer
Chapter
Part of the Topics in Organometallic Chemistry book series (TOPORGAN, volume 6)

Abstract

Over the past two decades the asymmetric dihydroxylation (AD) and asymmetric aminohydroxylation (AA) of alkenes has attracted a great deal of attention. Many literature examples have demonstrated that good to excellent ees and yields can be obtained with a diverse range of alkenes. The ability to perform reactions on small to moderate scale has led to increased utilization in larger scale applications. This review highlights recent advances in the AD and AA pertaining to practical, large-scale and industrial applications.

Keywords

Asymmetric dihydroxylation Asymmetric aminohydroxylation Cinchona alkaloids Process development Scale up 

List of Abbreviations

AA

Asymmetric aminohydroxylation

ABS

Acrylonitrile-butadiene-styrene

AD

Asymmetric dihydroxylation

AQN

Anthraquinone

CMR

Chemzyme membrane reactor

DHQ

Dihydroquinine

DHQD

Dihydroquinidine

MC

Microencapsulation

NMO

4-Methylmorpholine N-oxide

PEG

Poly(ethylene glycol)

PEM

Phenoxyethoxymethyl-polystyrene

PHAL

Phthalazine

PHN

Phenanthryl

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Authors and Affiliations

  • Steven J. Mehrman
    • 1
    Email author
  • Ahmed F. Abdel-Magid
    • 1
  • Cynthia A. Maryanoff
    • 1
  • Bart P. Medaer
    • 2
  1. 1.Drug Evaluation-Chemical DevelopmentJohnson & Johnson Pharmaceutical Research and DevelopmentUSA
  2. 2.Drug Evaluation-Chemical DevelopmentJohnson & Johnson Pharmaceutical Research and DevelopmentBeerseBelgium

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