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Five‐ and Seven‐Membered Rings from Alkenyl(methoxy)carbene Complexes and Methyl Ketone Enolates
Author(s) -
Barluenga José,
Alonso Jorge,
Rodríguez Félix,
Fañanás Francisco J.
Publication year - 2000
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 - 10.1002/1521-3773(20000717)39:14<2459::aid-anie2459>3.0.co;2-e
Subject(s) - carbene , ketone , methyl vinyl ketone , chemistry , ring (chemistry) , methyl ketone , medicinal chemistry , ring size , stereochemistry , catalysis , organic chemistry
A 1,2‐Cr(CO) 5 migration induces cyclization of the products from the 1,2‐addition of methyl ketone enolates to alkenyl(methoxy)carbene complexes [Eq. (1)]. The size of the resulting ring depends on the substituents on the carbene complex: With α , β ‐disubstitution, five‐membered rings are formed diastereoselectively. By contrast, the reaction of β ‐substituted alkenylcarbene complexes with methyl vinyl ketone enolates leads diastereoselectively to seven‐membered rings.