Combining NHC-Cu and BrOnsted Base Catalysis: Enantioselective Allylic Substitution/Conjugate Additions with Alkynylaluminum Reagents and Stereospecific Isomerization of the Products to Trisubstituted Allenes

被引：75
作者：
Dabrowski, Jennifer A. [1 ]
Haeffner, Fredrik [1 ]
Hoveyda, Amir H. [1 ]
机构：
[1] Boston Coll, Merkert Chem Ctr, Dept Chem, Chestnut Hill, MA 02467 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 30期
关键词：
alkynylaluminum reagents; allenes; BrOnsted bases; copper; N-heterocyclic carbenes; ASYMMETRIC CONJUGATE ALKYNYLATION; ENANTIOENRICHED ALLENES; PROPARGYLIC PHOSPHATES; TERMINAL ALKYNES; CHIRAL ALLENES; ALLENYLATION; ALKYLATION; REARRANGEMENT; REACTIVITY; LITHIATION;
D O I：
10.1002/anie.201303501
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
All-catalytic route to trisubstituted allenes: The first examples of catalytic enantioselective allylic substitution reactions that involve alkyne-based nucleophiles and lead to products having tertiary stereogenic centers are followed by an exceptionally stereospecific amine-catalyzed isomerization to trisubstituted allenes (see picture; NHC=N-heterocyclic carbene). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：7694 / 7699
页数：6
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