KHSO4-mediated condensation reactions of tert-butanesulfinamide with aldehydes.: Preparation of tert-butanesulfinyl aldimines

被引：43

作者：

Huang, ZY ^{[1
]}

Zhang, M ^{[1
]}

Wang, Y ^{[1
]}

Qin, Y ^{[1
]}

机构：

[1] Sichuan Univ, W China Sch Pharm, Dept Chem Med Nat Prod, Chengdu 610041, Peoples R China

来源：

SYNLETT | 2005年 / 08期

关键词：

tert-butanesulfinamide; aldehyde; tert-butanesulfinyl aldimines; potassium hydrogen sulfate; condensation;

D O I：

10.1055/s-2005-865234

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically pure tert-butanesulfinyl aldimines 1 were prepared by direct condensation of chiral tert-butanesulfinamide 3 with aldehydes 2 in high yields in the presence of KHSO4. The main advantage of KHSO4 is that it is applicable to the condensation reactions of a variety of aldehydes, including electron deficient and electron rich (hetereo)aromatic aldehydes, as well as aliphatic aldehydes.

引用

页码：1334 / 1336

页数：3

共 21 条

[1] STUDIES ON THE PREPARATION AND REACTIONS OF TRITYLSULFENIMINES [J].

BRANCHAUD, BP .

JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (20) :3531-3538

[2] Asymmetric synthesis of aziridine 2-phosphonates from enantiopure sulfinimines (N-sulfinyl imines).: Synthesis of α-amino phosphonates [J].

Davis, FA ;

Wu, YZ ;

Yan, HX ;

McCoull, W ;

Prasad, KR .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (06) :2410-2419

[3] Asymmetric synthesis and properties of sulfinimines (thiooxime S-oxides) [J].

Davis, FA ;

Reddy, RE ;

Szewczyk, JM ;

Reddy, GV ;

Portonovo, PS ;

Zhang, HM ;

Fanelli, D ;

Reddy, RT ;

Zhou, P ;

Carroll, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2555-2563

[4] 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

[5] N-tert-Butanesulfinyl imines:: Versatile intermediates for the asymmetric synthesis of amines [J].

Ellman, JA ;

Owens, TD ;

Tang, TP .

ACCOUNTS OF CHEMICAL RESEARCH, 2002, 35 (11) :984-995

[6] Stereoselective synthesis of 1,2-disubstituted β-amino alcohols by nucleophilic addition to N-tert-butanesulfinyl α-alkoxyaldimines [J].

Evans, JW ;

Ellman, JA .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (26) :9948-9957

[7] Properly designed modular asymmetric synthesis for enantiopure sulfinamide auxiliaries from N-sulfonyl-1,2,3-oxathiazolidine-2-oxide agents [J].

Han, ZX ;

Krishnamurthy, D ;

Grover, P ;

Fang, QK ;

Senanayake, CH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (27) :7880-7881

[8] 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

[9] Asymmetric Mannich-type reactions for the synthesis of aspartic acid derivatives from chiral N-tert-butanesulfinylimino esters [J].

Jacobsen, MF ;

Skrydstrup, T .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (18) :7112-7114

[10] 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

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