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Cu(OTf) 2 as an Efficient and Dual‐Purpose Catalyst in the Regioselective Reductive Ring Opening of Benzylidene Acetals
Author(s) -
Shie ChiRung,
Tzeng ZhengHao,
Kulkarni Suvarn S.,
Uang BiingJiun,
Hsu ChingYun,
Hung ShangCheng
Publication year - 2005
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/anie.200462172
Subject(s) - regioselectivity , ring (chemistry) , borane , chemistry , catalysis , acetal , silane , dual (grammatical number) , medicinal chemistry , combinatorial chemistry , organic chemistry , philosophy , linguistics
Reducing the choices . Cu(OTf) 2 is an efficient and dual‐purpose catalyst for the highly regioselective reductive ring openings of benzylidene acetals with either BH 3 or Me 2 EtSiH to give the corresponding primary and secondary alcohols (see scheme). Isotope studies have confirmed that both modes of ring cleavage proceed by an S N 1 reaction pathway when borane or silane attack the acetal carbon center.