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Enhancement of 1,2‐Asymmetric Induction on CC Linkage by Use of Chiral 2‐Butenylboronic Esters
Author(s) -
Hoffmann Reinhard W.,
Zeiss HansJoachim
Publication year - 1980
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.198002181
Subject(s) - reagent , aldehyde , asymmetric induction , chemistry , chiral derivatizing agent , linkage (software) , preference , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , enantiomer , catalysis , chiral column chromatography , mathematics , biochemistry , statistics , gene
Combination of chiral aldehyde (1) and chiral reagent (2) (derived from 2‐ exo ‐3‐ exo ‐dihydroxy‐3‐ endo ‐phenylbornane) permitted a diastereoselectivity of ca. 11:1 in the formation of alcohols (3) and (4) . Cram preference and chiral control by the reagent reinforce each other.