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Synthesis of Enantioenriched 5‐Alkylidene‐2‐cyclopentenones from Chiral Allenyl Carbamates: Generation of a Chiral Lithium Allenolate and Allylic Activation for a Conrotatory 4π‐Electrocyclization
Author(s) -
SchultzFademrecht Carsten,
Tius Marc A.,
Grimme Stefan,
Wibbeling B.,
Hoppe Dieter
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 - 10.1002/1521-3773(20020503)41:9<1532::aid-anie1532>3.0.co;2-j
Subject(s) - conrotatory and disrotatory , lithium (medication) , allylic rearrangement , chemistry , organic chemistry , ring (chemistry) , biology , catalysis , endocrinology
A stereospecific ring‐closure reaction takes place between chiral allenyl carbamates and enones. After lithiation, carbonyl addition, and subsequent carbamoyl (Cb = CON i Pr 2 ) group migration (see scheme), a stereospecific conrotatory cyclization leads to 5‐alkylidene‐2‐cyclopentenones.