Highly efficient deprotection of N-p-toluenesulfinyl group of β-branched Baylis-Hillman adducts by using amberlite IR-120 (plus) ion-exchange resin

被引：18

作者：

Li, GG ^{[1
]}

Kim, SH ^{[1
]}

Wei, HX ^{[1
]}

机构：

[1] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

TETRAHEDRON | 2000年 / 56卷 / 05期

关键词：

Baylis-Hillman adducts; N-p-toluenesulfinyl cleavage; Amberlite 1R-120 (plus) resin;

D O I：

10.1016/S0040-4020(99)01064-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient deprotection of N-p-toluenesulfinyl group of beta-branched Baylis-Hillman adducts has been developed by using Amberlite IR-120 (plus) ion-exchange resin in methanol solution at room temperature. Good to quantitative yields have been obtained for six examples. No racemization was detected under the mild conditions. This new method provides a simultaneous deprotection/purification, which has the great advantage over the solution phase deprotection technique of simplicity of work-up. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：719 / 723

页数：5

共 34 条

[1]

[Anonymous], 1994, Aldrichimica Acta

[2] Sulfinimines of trifluoropyruvate:: Novel intermediates for chiral non racemic α-trifluoromethyl α-amino acids [J].

Bravo, P ;

Crucianelli, M ;

Vergani, B ;

Zanda, M .

TETRAHEDRON LETTERS, 1998, 39 (42) :7771-7774

[3] Synthesis of tetrasubstituted ethylenes on solid support via resin capture [J].

Brown, SD ;

Armstrong, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (26) :6331-6332

[4] Asymmetric synthesis of α,α-dibranched amines by the trimethylaluminum-mediated 1,2-addition of organolithiums to tert-butanesulfinyl ketimines [J].

Cogan, DA ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) :268-269

[5] Synthesis and applications of nonracemic β-amino aldehydes to the asymmetric synthesis of piperdines:: (+)-dihydropinidine [J].

Davis, FA ;

Szewczyk, JM .

TETRAHEDRON LETTERS, 1998, 39 (33) :5951-5954

[6] Sulfinimine-mediated asymmetric synthesis of (R)-(4-methoxy-3,5-dihydroxyphenyl)glycine: The central amino acid of vancomycin and related agents [J].

Davis, FA ;

Fanelli, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (06) :1981-1985

[7] Aziridine 2-carboxylate ester mediated asymmetric synthesis of alpha-alkyl beta-amino acids [J].

Davis, FA ;

Reddy, GV ;

Liang, CH .

TETRAHEDRON LETTERS, 1997, 38 (29) :5139-5142

[8] ASYMMETRIC-SYNTHESIS OF 2H-AZIRINES - FIRST ENANTIOSELECTIVE SYNTHESIS OF THE CYTOTOXIC ANTIBIOTIC (R)-(-)-DYSIDAZIRINE [J].

DAVIS, FA ;

REDDY, GV ;

LIU, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (12) :3651-3652

[9] Asymmetric synthesis of beta-substituted alpha-amino acids using 2H-azirine-2-carboxylate esters. Synthesis of 3,3-disubstituted aziridine-2-carboxylate esters [J].

Davis, FA ;

Liang, CH ;

Liu, H .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (12) :3796-3797

[10] Improved synthesis of enantiopure sulfinimines (thiooxime S-oxides) from p-toluenesulfinamide and aldehydes and ketones [J].

Davis, FA ;

Zhang, YL ;

Andemichael, Y ;

Fang, TA ;

Fanelli, DL ;

Zhang, HM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (04) :1403-1406

← 1 2 3 4 →