High Stereoselectivity in Lewis‐Acid‐Catalyzed and Uncatalyzed Diels–Alder Reactions of the Fumarate of (S)‐Ethyl Lactate | Zendy

Hartmann Horst | Zendy; Hady Abdel Fattah Abdel | Zendy; Sartor Karina | Zendy; Weetman John | Zendy; Helmchen Günter | Zendy

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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].

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