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Stereoselective synthesis of alcohols, XXVIII. Stereocontrol of addition of chiral ( E )‐(α‐chlorocrotyl)boronates to chiral aldehydes
Author(s) -
Hoffmann Reinhard W.,
Dresely Stefan,
Hildebrandt Bernhard
Publication year - 1988
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.19881211222
Subject(s) - chemistry , aldehyde , stereochemistry , stereoselectivity , asymmetric induction , enantioselective synthesis , reagent , optically active , catalysis , organic chemistry
Abstract On reaction of the chiral ( E )‐(α‐chlorocrotyl)boronates 5 with chiral aldehydes 1 , the diastereoselectivity depends on whether the asymmetric induction of the reagent and the substrate cooperate (matched pair) or whether they are opposed (mismatched pair). In the first situation, very high diastereoselectivity in favor of the products 2 with the stereotriade C was realized. In the second case, reagent control of stereoselectivity in favor of the products 3 with the stereotriade D was possible only if the asymmetric induction of the aldehyde 1 corresponded to a ΔΔ G ≠of ≤1 kcal.