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Highly Diastereoselective Synthesis of Monocyclic and Bicyclic Secondary Diorganozinc Reagents with Defined Configuration
Author(s) -
Boudier Andreas,
Hupe Eike,
Knochel Paul
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(20000703)39:13<2294::aid-anie2294>3.0.co;2-j
Subject(s) - transmetalation , hydroboration , stereocenter , reagent , electrophile , bicyclic molecule , chemistry , substrate (aquarium) , combinatorial chemistry , boron , stereochemistry , sequence (biology) , organic chemistry , enantioselective synthesis , catalysis , biology , ecology , biochemistry
Configurationally stable secondary diorganozinc reagents with three adjacent stereocenters can be prepared with high diastereoselectivity by a reaction sequence comprising a substrate‐controlled hydroboration and a boron–zinc exchange (see scheme). After a second transmetalation numerous cyclic products are accessible by reaction with various electrophiles.