The N-hydroxymethyl group for stereoselective conjugate addition: application to the synthesis of (-)-statine

Dongwon Yoo; Joon Seok Oh; Young Gyu Kim

doi:10.1021/ol025653u

The N-hydroxymethyl group for stereoselective conjugate addition: application to the synthesis of (-)-statine

Org Lett. 2002 Apr 4;4(7):1213-5. doi: 10.1021/ol025653u.

Authors

Dongwon Yoo¹, Joon Seok Oh, Young Gyu Kim

Affiliation

¹ School of Chemical Engineering, College of Engineering, Seoul National University, Seoul 151-744, Korea.

PMID: 11922821
DOI: 10.1021/ol025653u

Abstract

[reaction: see text] Efficient synthesis of enantiomerically pure (-)-statine was achieved with the stereoselective intramolecular conjugate addition of the hydroxyl group tethered to the amino group of a configurationally stable N-Boc-L-leucinal derivative.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemical synthesis*
Cyclization
Hydrolysis
Hydroxides / chemistry
Indicators and Reagents
Potassium Compounds / chemistry
Stereoisomerism

Substances

Amino Acids
Hydroxides
Indicators and Reagents
Potassium Compounds
potassium hydroxide
statine