Spirocyclization of Isatin with Chiral α-Aminothiols: Diastereoselective Synthesis of (-)- and (+)-4'-(Methoxycarbonyl)spiro[indoline-3,2'-thiazolidin]-2-one

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Title:Spirocyclization of Isatin with Chiral α-Aminothiols: Diastereoselective Synthesis of (-)- and (+)-4'-(Methoxycarbonyl)spiro[indoline-3,2'-thiazolidin]-2-one
Creators:
Kutschy, Peter
Suchý, Mojmír
Dzurilla, Milan
Pazdera, Pavel
Takasugi, Mitsuo
Kováčik, Vladimír
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 65, 3, pp. 425-433
Uncontrolled Keywords:Phytoalexins, Indoles, Thiazolidines, Penicillamine, Cysteine, Diastereoselective spirocyclization

Abstract

Reactions of isatin with chiral α-aminothiols have been studied. With L-cysteine, only decomposition products were formed under various reaction conditions, whereas D- and L-penicillamine afforded mixtures of diastereomeric 4'-carboxy-5',5'-dimethylspiro[indoline- 3,2'-thiazolidin]-2-ones (<strong>4a</strong> and <strong>4b</strong> or <strong>5a</strong> and <strong>5b</strong>) in the ratio 1 : 1. The reaction of isatin with methyl L- and D-cysteinates under mild reaction conditions (methanol-benzene, room temperature) proceeded diastereoselectively with the formation of (-)- and (+)-4'-(methoxycarbonyl)spiro[indoline-3,2'-thiazolidin]-2-one (<strong>6a</strong> and <strong>8</strong>) in 38 and 30% yields, respectively. Optically inactive 4'-(methoxycarbonyl)spiro[indoline-3,2'-([2',5']dihydrothiazol)]-2-one (<strong>7</strong>) was isolated as a side product in 7 and 3% yield, respectively. Structure of the obtained products was determined by spectral methods, including NOE difference measurements and by X-ray crystallography.

Title:Spirocyclization of Isatin with Chiral α-Aminothiols: Diastereoselective Synthesis of (-)- and (+)-4'-(Methoxycarbonyl)spiro[indoline-3,2'-thiazolidin]-2-one
Creators:
Kutschy, Peter
Suchý, Mojmír
Dzurilla, Milan
Pazdera, Pavel
Takasugi, Mitsuo
Kováčik, Vladimír
Uncontrolled Keywords:Phytoalexins, Indoles, Thiazolidines, Penicillamine, Cysteine, Diastereoselective spirocyclization
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:65
Number:3
Page Range:pp. 425-433
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20000425UNSPECIFIED
ID Code:1652
Item Type:Article
Deposited On:06 Feb 2009 17:11
Last Modified:06 Feb 2009 16:11

Citation

Kutschy, Peter; Suchý, Mojmír; Dzurilla, Milan; Pazdera, Pavel; Takasugi, Mitsuo; Kováčik, Vladimír (2000) Spirocyclization of Isatin with Chiral α-Aminothiols: Diastereoselective Synthesis of (-)- and (+)-4'-(Methoxycarbonyl)spiro[indoline-3,2'-thiazolidin]-2-one. Collection of Czechoslovak Chemical Communications, 65 (3). pp. 425-433. ISSN 0010-0765

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