STEREOSELECTIVE REDUCTION OF ENAMINO SULFOXIDES

被引：13

作者：

OGURA, K

TOMORI, H

FUJITA, M

机构：

来源：

CHEMISTRY LETTERS | 1991年 / 08期

关键词：

D O I：

10.1246/cl.1991.1407

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Enamino sulfoxides, p-TolS(O)CH = C(NR1R2)R (where R1 = alkyl, R2 = H or alkyl), were reduced with lithium tri(s-butyl)borohydride or borane.THF, respectively, to give beta-amino sulfoxides of R*,R* configuration with high stereoselectivity.

引用

页码：1407 / 1410

页数：4

共 17 条

[1] STEREOSELECTIVE REDUCTIONS OF 2-KETO SULFOXIDES WITH HYDRIDES [J].

CARRENO, MC ;

RUANO, JLG ;

MARTIN, AM ;

PEDREGAL, C ;

RODRIGUEZ, JH ;

RUBIO, A ;

SANCHEZ, J ;

SOLLADIE, G .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2120-2128

[2]

DESLONGCHAMPS P, 1983, STEREOELECTRONIC EFF, pCH6

[3] ASYMMETRIC TOTAL SYNTHESES OF ELAEOKANINE-A AND ELAEOKANINE-B VIA ALPHA-SULFINYL KETIMINE [J].

HUA, DH ;

BHARATHI, SN ;

ROBINSON, PD ;

TSUJIMOTO, A .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (07) :2128-2132

[4] Walden inversion reactions of d-beta-Butyl, d-beta-octyl, and d-benzylmethylcarbinyl p-toluenesulphonates. [J].

Kenyon, J ;

Phillips, H ;

Pittman, VP .

JOURNAL OF THE CHEMICAL SOCIETY, 1935, :1072-1084

[5] HIGHLY ENANTIOSELECTIVE REARRANGEMENT OF (S)-E-ALPHA-PARA-TOLYLSULPHINYL-ALPHA,BETA-ENOATES TO (R)-E-GAMMA-HYDROXY-ALPHA,BETA-ENOATES [J].

KOSUGI, H ;

KITAOKA, M ;

TAKAHASHI, A ;

UDA, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (16) :1268-1270

[6] STEREOSELECTIVE REACTIONS OF (+)-(R)-ALPHA(P-TOLYLSULFINYL)ACETOPHENONE WITH ALKYL GRIGNARD-REAGENTS IN ETHYL ETHER [J].

KUNIEDA, N ;

NOKAMI, J ;

KINOSHIT.M .

CHEMISTRY LETTERS, 1974, (04) :369-372

[7] A PRACTICAL OPTICAL RESOLUTION OF (ARYLSULFINYL)ACETONES AND ITS APPLICATION TO THE SYNTHESIS OF 2-(ARYLSULFINYL)CYCLOALKANONES [J].

OGURA, K ;

ISHIDA, M ;

TOMORI, H ;

FUJITA, M .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1989, 62 (11) :3531-3536

[8] AN EFFICIENT 1,3-ASYMMETRIC INDUCTION ACCOMPANIED WITH EPIMERIZATION AT THE 2-POSITION - STEREOSELECTIVE REDUCTION OF ALPHA-SUBSTITUTED BETA-KETO SULFOXIDES UNDER BASIC CONDITIONS [J].

OGURA, K ;

FUJITA, M ;

INABA, T ;

TAKAHASHI, K ;

IIDA, H .

TETRAHEDRON LETTERS, 1983, 24 (05) :503-506

[9] TOTAL SYNTHESIS OF FURANETHER-B [J].

PRICE, ME ;

SCHORE, NE .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (24) :5662-5667

[10] ASYMMETRIC ADDITIONS OF ALPHA-SULFOXIDE CARBANION ON IMINES [J].

RONAN, B ;

MARCHALIN, S ;

SAMUEL, O ;

KAGAN, HB .

TETRAHEDRON LETTERS, 1988, 29 (47) :6101-6104

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