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Enantiopure β‐Hydroxy Morpholine Amides from Terminal Epoxides by Carbonylation at 1 atm
Author(s) -
Goodman Steven N.,
Jacobsen Eric N.
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200290022
Subject(s) - enantiopure drug , carbonylation , morpholine , chemistry , combinatorial chemistry , organic chemistry , reductase , stereochemistry , catalysis , enzyme , enantioselective synthesis , carbon monoxide
Keeping the CO pressure down is a crucial, practical feature of the new methodology for the carbonylation of terminal epoxides. β‐Hydroxy morpholinyl amides are generated directly in optically pure form [Eq. (1)], and these building blocks can be applied in a variety of acyl transfer reactions. A useful illustration is provided in the concise synthesis of δ‐hydroxy‐β‐ketoesters, key intermediates for the preparation of the statin class of HMG‐CoA reductase inhibitors.