Open AccessUnexpected reversal of stereochemistry observed in the addition of methallyltrimethylsilane to a chiral α-keto imide
Author(s) -
Sayaka Ishii,
Katsuya Saito,
Shigefumi Kuwahara,
Masaru Enomoto
Publication year - 2021
Publication title -
bioscience biotechnology and biochemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.509
H-Index - 116
eISSN - 1347-6947
pISSN - 0916-8451
DOI - 10.1093/bbb/zbaa086
Subject(s) - imide , stereoselectivity , selectivity , lewis acids and bases , chemistry , stereochemistry , nucleophile , organic chemistry , catalysis
A Lewis acid–promoted nucleophilic addition of methallyltrimethylsilane to a chiral α-keto imide proceeded with stereoselectivity opposite to that predicted from Soai's report. The difference in the structure of α-keto imides between Soai's and our cases might have affected the diastereofacial selectivity.
Accelerating Research
Robert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom
Address
John Eccles HouseRobert Robinson Avenue,
Oxford Science Park, Oxford
OX4 4GP, United Kingdom