Highly 2,3-trans stereoselective allylations of 2, 3-O-isopropylidene-protected pyrrolidines: circumventing the N-acyliminium ion chemistry?

P de Armas; F García-Tellado; J J Marrero-Tellado

doi:10.1021/ol006574q

Highly 2,3-trans stereoselective allylations of 2, 3-O-isopropylidene-protected pyrrolidines: circumventing the N-acyliminium ion chemistry?

Org Lett. 2000 Nov 2;2(22):3513-5. doi: 10.1021/ol006574q.

Authors

P de Armas¹, F García-Tellado, J J Marrero-Tellado

Affiliation

¹ Instituto de Productos Naturales y Agrobiología-CSIC, Astrofísico Francisco Sánchez 3, 38206 La Laguna-Tenerife, Spain. [email protected]

PMID: 11082022
DOI: 10.1021/ol006574q

Abstract

[reaction: see text] A remarkable exo-facial template effect exercised by a 2, 3-O-isopropylidene protective group is the key for the entire 2, 3-trans stereoselectivity observed in the allylsilane addition promoted by BF(3).OEt(2) to 2,3-O-isopropylidene-protected pyrrolidines.

Publication types

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

MeSH terms

Drug Design
Imines
Indicators and Reagents
Molecular Conformation
Molecular Structure
Pyrrolidines / chemical synthesis*
Stereoisomerism

Substances

Imines
Indicators and Reagents
Pyrrolidines