Catalytic Enantioselective Synthesis of Chiral Isatin Derivatives by an Aldol Approach

Akira Yanagisawa; Naoyuki Kushihara; Takuya Sugita; Kazuhiro Yoshida

doi:10.1055/s-0032-1316551

Synlett, Table of Contents

Synlett 2012; 23(12): 1783-1788
DOI: 10.1055/s-0032-1316551

letter

Catalytic Enantioselective Synthesis of Chiral Isatin Derivatives by an Aldol Approach

Akira Yanagisawa*

Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan, Fax: +81(43)2902789 Email: ayanagi@faculty.chiba-u.jp

,

Naoyuki Kushihara

Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan, Fax: +81(43)2902789 Email: ayanagi@faculty.chiba-u.jp

,

Takuya Sugita

Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan, Fax: +81(43)2902789 Email: ayanagi@faculty.chiba-u.jp

,

Kazuhiro Yoshida

Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan, Fax: +81(43)2902789 Email: ayanagi@faculty.chiba-u.jp

› Author Affiliations

Abstract

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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.

Key words

aldol reaction - alkenyl ester - asymmetric catalysis - isatin - tin

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