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Synlett 2012; 23(12): 1783-1788
DOI: 10.1055/s-0032-1316551
DOI: 10.1055/s-0032-1316551
letter
Catalytic Enantioselective Synthesis of Chiral Isatin Derivatives by an Aldol Approach
Further Information
Publication History
Received: 16 April 2012
Accepted after revision: 23 May 2012
Publication Date:
29 June 2012 (online)
Abstract
A catalytic enantioselective aldol reaction of alkenyl esters with isatins was achieved using an (S)-BINOL-derived chiral tin dibromide possessing a 4-tert-butylphenyl group at 3- and 3′-positions as the chiral pre-catalyst in the presence of sodium methoxide and methanol. Optically active 3-alkylated 3-hydroxy-2-oxindoles having up to 98% ee were diastereoselectively obtained in high yields not only from cyclic alkenyl esters but also from acyclic ones under the influence of the in situ generated chiral tin bromide methoxide.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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