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Molybdenum‐Catalyzed Asymmetric Allylic Alkylation of 3‐Alkyloxindoles: Reaction Development and Applications
Author(s) -
Trost Barry M.,
Zhang Yong
Publication year - 2011
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/chem.201002569
Subject(s) - nucleophile , alkylation , tsuji–trost reaction , catalysis , oxindole , indoline , chemistry , molybdenum , combinatorial chemistry , organic chemistry , allylic rearrangement
We report a full account of our work towards the development of Mo‐catalyzed asymmetric allylic alkylation reactions with 3‐alkyloxindoles as nucleophiles. The reaction is complementary to the Pd‐catalyzed reaction with regard to the scope of oxindole nucleophiles. A number of 3‐alkyloxindoles were alkylated successfully under mild conditions to give products with excellent yields and good‐to‐excellent enantioselectivities. Applications of this method to the preparation of indoline alkaloids such as (−)‐physostigmine, ent‐ (−)‐debromoflustramine B, and the indolinoquinoline rings of communesin B are reported.