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High Stereoselectivity in Lewis‐Acid‐Catalyzed and Uncatalyzed Diels–Alder Reactions of the Fumarate of (S)‐Ethyl Lactate
Author(s) -
Hartmann Horst,
Hady Abdel Fattah Abdel,
Sartor Karina,
Weetman John,
Helmchen Günter
Publication year - 1987
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.198711431
Subject(s) - diastereomer , ethyl lactate , cyclopentadiene , chemistry , stereoselectivity , catalysis , enantiomer , lewis acids and bases , diels–alder reaction , organic chemistry , medicinal chemistry
Enantiomeric diastereomers can be selectively obtained from the fumarate 1 and dienes. For instance, the uncatalyzed Diels‐Alder reaction of 1 with cyclopentadiene gives preferentially the diastereomer 2a ( 2a : 2b = 98 :2); with TiCl 4 as catalyst, on the other hand, 2b is the main product ( 2a : 2b = 5 :95). Analogous results were obtained for less reactive dienes [R * OH = ( S )‐ethyl lactate].