Racemization Free Protocol for the Synthesis of N-tert-Butanesulfinyl Ketimines

被引：23

作者：

Datta, Gopal K. ^{[2
]}

Ellman, Jonathan A. ^{[1
]}

机构：

[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA

[2] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 18期

基金：

美国国家科学基金会;

关键词：

ASYMMETRIC-SYNTHESIS; DIRECT CONDENSATION; FACILE SYNTHESIS; SULFINIMINES; ALDEHYDES; SULFINAMIDES; IMINES; ALDIMINES; AMINES;

D O I：

10.1021/jo1011625

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general and robust racemization-free protocol for the synthesis of a variety of N-tert-butanesulfinyl ketimines is reported. Reaction progress was monitored by H-1 NMR using the nonperturbing internal standard diglyme, and ketimines were formed in good to high yields in either THF or CPME (cyclopentyl methyl ether) as solvent with heating to reflux.

引用

收藏

页码：6283 / 6285

页数：3

相关论文

共 16 条

[1] A facile synthesis of N-sulfinylaldimines [J].

Ardej-Jakubisiak, Monika ;

Kawecki, Robert ;

Swietlinska, Aneta .

TETRAHEDRON-ASYMMETRY, 2007, 18 (21) :2507-2509

[2] STEREOCHEMISTRY OF SULFUR-COMPOUNDS .3. RADICAL-CHAIN MECHANISM FOR RACEMIZATION OF SULFINAMIDES [J].

BOOMS, RE ;

CRAM, DJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (15) :5438-&

[3] 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

[4] Reversal of diastereofacial selectivity in hydride reductions of N-tert-butanesulfinyl imines [J].

Colyer, John T. ;

Andersen, Neil G. ;

Tedrow, Jason S. ;

Soukup, Troy S. ;

Faul, Margaret M. .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18) :6859-6862

[5] A facile synthesis of N-sulfonyl and N-sulfinyl aldimines under Barbier-type conditions [J].

Fan, Renhua ;

Pu, Dongming ;

Wen, Fengqi ;

Ye, Yang ;

Wang, Xiaoli .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3623-3625

[6] tert-Butanesulfinimines: structure, synthesis and synthetic applications [J].

Ferreira, Franck ;

Botuha, Candice ;

Chemla, Fabrice ;

Perez-Luna, Alejandro .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (04) :1162-1186

[7] Synthesis of sulfinimines by direct condensation of sulfinamides with aldehydes using Cs2CO3 as an activating and dehydrating reagent [J].

Higashibayashi, S ;

Tohmiya, H ;

Mori, T ;

Hashimoto, K ;

Nakata, M .

SYNLETT, 2004, (03) :457-460

[8] KHSO4-mediated condensation reactions of tert-butanesulfinamide with aldehydes.: Preparation of tert-butanesulfinyl aldimines [J].

Huang, ZY ;

Zhang, M ;

Wang, Y ;

Qin, Y .

SYNLETT, 2005, (08) :1334-1336

[9] Synthesis of enantiopure sulfinimines (thiooxime S-oxides) catalyzed by Yb(OTf)3 from p-toluenesulfinamide and aldehydes in mild reaction conditions [J].

Jiang, ZY ;

Chan, WH ;

Lee, AWM .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (03) :1081-1083

[10] Catalytic asymmetric synthesis of tert-butanesulfinamide. Application to the asymmetric synthesis of amines [J].

Liu, GC ;

Cogan, DA ;

Ellman, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (41) :9913-9914