Toward a versatile allylation reagent: practical, enantioselective allylation of acylhydrazones using strained silacycles

Richard Berger; Philippe M A Rabbat; James L Leighton

doi:10.1021/ja035001g

Toward a versatile allylation reagent: practical, enantioselective allylation of acylhydrazones using strained silacycles

J Am Chem Soc. 2003 Aug 13;125(32):9596-7. doi: 10.1021/ja035001g.

Authors

Richard Berger¹, Philippe M A Rabbat, James L Leighton

Affiliation

¹ Department of Chemistry, Columbia University, New York, New York 10027, USA.

PMID: 12904019
DOI: 10.1021/ja035001g

Abstract

A highly practical method for the enantioselective allylation of acylhydrazones has been developed. The previously reported strained silacycle reagent 1 reacts with a wide variety of acylhydrazones to give the hydrazide products with good enantioselectivity (83-89% ee, typically). It has been demonstrated that the products may be isolated without chromatography by recrystallization in >/=98% ee.

Publication types

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

MeSH terms

Allyl Compounds / chemical synthesis*
Allyl Compounds / chemistry
Hydrazones / chemistry*
Imines / chemistry
Silanes / chemistry*
Stereoisomerism

Substances

Allyl Compounds
Hydrazones
Imines
Silanes