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The Dienolate of ( R )‐2‐ tert ‐Butyl‐6‐methyl‐1,3‐dioxin‐4(2 H )‐one—a Chiral Acetoacetic Ester d 4 ‐Reagent
Author(s) -
Seebach Dieter,
Misslitz Ulf,
Uhlmann Peter
Publication year - 1989
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.198904721
Subject(s) - reagent , chemistry , methylene , medicinal chemistry , acetoacetic ester synthesis , carbonyl group , stereochemistry , organic chemistry
The dienolate 2, M = Li, Na, K, SiR 3 , readily generated from 1, is a very promising synthetic equivalent of the acetoacetic ester dianion. Compound 2 reacts with aldehydes and ketones at C‐5 or at the exocyclic methylene group, depending on the conditions, and with α,β‐unsaturated carbonyl compounds by Michael addition. Surprisingly, some of these reactions proceed with a diastereoselectivity of > 20:1.