Premium
Stereoselective synthesis of alcohols, XIX. The sense of asymmetric induction on addition to α‐chiral aldehydes
Author(s) -
Hoffmann Reinhard W.,
Weidmann Ulrich
Publication year - 1985
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19851181010
Subject(s) - chemistry , asymmetric induction , stereoselectivity , reagent , preference , sense (electronics) , organic chemistry , aldehyde , stereochemistry , enantioselective synthesis , catalysis , economics , microeconomics
On addition of ( E )‐crotylboronates to aldehydes with an α‐methyl branch the expected Cram‐products are formed predominantly. On addition of the ( Z )‐crotylboronates to the same aldehydes the anti‐Cram‐products are formed in preference. Hence, the sense of 1,2‐asymmetric induction depends also on the nature of the achiral reagent. The reasons for and the conditions leading to such a phenomenon are discussed.