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Substrate‐Controlled Highly Diastereoselective Synthesis of Primary and Secondary Diorganozinc Reagents by a Hydroboration/Boron–Zinc Exchange Sequence
Author(s) -
Hupe Eike,
Calaza M. Isabel,
Knochel Paul
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200204662
Subject(s) - hydroboration , chemistry , reagent , zinc , electrophile , substrate (aquarium) , boron , combinatorial chemistry , organic chemistry , primary (astronomy) , catalysis , oceanography , physics , astronomy , geology
The scope of substrate‐controlled diastereoselective hydroborations can be considerably enhanced by a boron–zinc exchange reaction, providing organozinc derivatives that react with a broad range of electrophiles. Even normally unreactive boronic esters, obtained by Rh‐catalyzed hydroboration with catecholborane, react readily with i Pr 2 Zn providing the corresponding zinc reagents in high diastereoselectivity.