Cu(OTf) 2  as an Efficient and Dual‐Purpose Catalyst in the Regioselective Reductive Ring Opening of Benzylidene Acetals | Zendy

Shie ChiRung | Zendy; Tzeng ZhengHao | Zendy; Kulkarni Suvarn S. | Zendy; Uang BiingJiun | Zendy; Hsu ChingYun | Zendy; Hung ShangCheng | Zendy

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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.

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