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Stereoselective Preparation and Reactions of Configurationally Defined Dialkylzinc Compounds
Author(s) -
Boudier Andreas,
Darcel Christophe,
Flachsmann Felix,
Micouin Laurent,
Oestreich Martin,
Knochel Paul
Publication year - 2000
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 - 10.1002/1521-3765(20000804)6:15<2748::aid-chem2748>3.0.co;2-q
Subject(s) - reagent , electrophile , chemistry , stereoselectivity , zinc , combinatorial chemistry , boron , optically active , reaction conditions , organic chemistry , catalysis
The reaction of cyclic and open‐chain diastereomerically pure secondary organoboranes with diisopropylzinc allows the preparation of secondary dialkylzinc reagents with good to excellent retention of configuration as shown by deuterolysis and Cu I ‐ and Pd 0 ‐mediated reactions with electrophiles. The importance of a high boron‐zinc exchange rate to obtain high diastereoselectivity has been shown. Improvement of the configurational stability and stereomeric purity of the zinc intermediates has been obtained by using mono‐isopinocampheylborane ((−)‐IpcBH 2 ) providing optically active dialkylzinc compounds (up to 96 % ee ) with enhanced diastereoselectivities.