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Formal Enantioselective Michael Addition with Umpolung of Reactivity
Author(s) -
Hupe Eike,
Knochel Paul
Publication year - 2001
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(20010817)40:16<3022::aid-anie3022>3.0.co;2-w
Subject(s) - umpolung , transmetalation , enantioselective synthesis , hydroboration , chemistry , michael reaction , formal synthesis , reactivity (psychology) , boron , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , nucleophile , medicine , alternative medicine , pathology
By a sequence comprising asymmetric hydroboration, boron–zinc exchange, and transmetalation with copper, allylations, alkynylations, and allenylations of unsaturated ketals or acetals can be performed with good enantioselectivities (see scheme, (−)‐IpcBH 2 =(−)‐isopinocampheylborane, TMS=Me 3 Si). The products correspond to a formal Michael addition with inversion of polarity.