Premium
Reaction of the Carbanions of 2‐(Alkylthio)thiolane 1‐Oxides with Oxiranes
Author(s) -
Schuler Barbara,
Adiwidjaja Gunadi,
Voss Jürgen
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199906)1999:6<1481::aid-ejoc1481>3.0.co;2-c
Subject(s) - carbanion , chemistry , stereoselectivity , enantiomer , medicinal chemistry , epoxide , organic chemistry , computational chemistry , stereochemistry , catalysis
Carbanions of the 2‐(alkylthio)thiolane 1‐oxides 1 and 2 are generated and subjected to reaction with the epoxides 3–5 . The resulting carbinols 6–11 are formed with high α diastereoselectivity, which is explained by a stabilization of the trans configuration of the carbanions in the activated complex. A minor γ stereoselectivity is also observed in case of the reactions with 4 and 5 . The pure enantiomers (1 S ,2 S ,2′ S )‐ 9a and (1 R ,2 R ,2′ S )‐ 11b were obtained from 2 and ( S )‐ 4 or ( R )‐ 5 , respectively, and their configurations were proved by X‐ray structural analyses.