Synlett 2015; 26(18): 2541-2546
DOI: 10.1055/s-0035-1560636
letter
© Georg Thieme Verlag Stuttgart · New York

Catalytic Enantioselective Synthesis of Chiral 3-Amino-2-oxindoles by a Mannich Approach

Akira Yanagisawa*
Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan   eMail: ayanagi@faculty.chiba-u.jp
,
Naoyuki Kushihara
Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan   eMail: ayanagi@faculty.chiba-u.jp
,
Takuya Sugita
Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan   eMail: ayanagi@faculty.chiba-u.jp
,
Moe Horiguchi
Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan   eMail: ayanagi@faculty.chiba-u.jp
,
Kazuki Ida
Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan   eMail: ayanagi@faculty.chiba-u.jp
,
Kazuhiro Yoshida
Department of Chemistry, Graduate School of Science, Chiba University, Inage, Chiba 263-8522, Japan   eMail: ayanagi@faculty.chiba-u.jp
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Publikationsverlauf

Received: 17. Juni 2015

Accepted after revision: 31. August 2015

Publikationsdatum:
29. September 2015 (online)


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Abstract

A catalytic enantioselective Mannich-type reaction of a cyclohexanone-derived alkenyl trichloroacetate with isatin imines was achieved using an (S)-BINOL-derived chiral tin dibromide possessing a 4-tert-butylphenyl group at 3- and 3′-positions as the chiral precatalyst in the presence of sodium methoxide, sodium iodide, and methanol. Optically active 3-alkylated 3-amino-2-oxindoles having up to 90% enantiomeric excess were diastereoselectively obtained in high yields under the influence of the in situ generated chiral tin iodide methoxide.

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