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Catalytic and Stoichiometric Enantioselective Addition of Diethylzinc to Aldehydes Using a Novel Chiral Spirotitanate
Author(s) -
Schmidt Beat,
Seebach Dieter
Publication year - 1991
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199100991
Subject(s) - diethylzinc , stoichiometry , enantioselective synthesis , catalysis , aldehyde , chemistry , organic chemistry
Simple variation of the reaction conditions in the addition of Et 2 Zn to aldehydes in the presence of spirotitanate 1 can lead to a reversal in the configuration of the product. Stoichiometric amounts of the spirotitanate result in Re addition of Et 2 Zn to the aldehyde (up to 98% ee ). In the presence of equimolar amounts of Ti(OCHMe 2 ) 4 , catalytic amounts of 1 lead to Si addition of Et 2 Zn (up to 99% ee ).
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