Direct reductive amination of aldehydes and ketones using phenylsilane: Catalysis by dibutyltin dichloride

被引：166

作者：

Apodaca, R ^{[1
]}

Xiao, W ^{[1
]}

机构：

[1] RW Johnson Pharmaceut Res Inst, San Diego, CA 92121 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 11期

关键词：

D O I：

10.1021/ol015948s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A procedure for direct reductive amination of aldehydes and ketones was developed which uses phenylsilane as a stoichiometric reductant and dibutyltin dichloride as a catalyst. Suitable amines included anilines and dialkylamines but not monoalkylamines.

引用

页码：1745 / 1748

页数：4

共 30 条

[21]

Shibata I, 1998, SYNLETT, P1081

[22] Chemoselective reductions of imino groups by dibutyltin chloride hydride complex [J].

Shibata, I ;

Moriuchi-Kawakami, T ;

Tanizawa, D ;

Suwa, T ;

Sugiyama, E ;

Matsuda, H ;

Baba, A .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (02) :383-385

[23] IMINE SYNTHESIS IN STRICTLY NEUTRAL CONDITIONS [J].

STETIN, C ;

DEJESO, B ;

POMMIER, JC .

SYNTHETIC COMMUNICATIONS, 1982, 12 (07) :495-499

[24]

Suwa T, 2000, SYNTHESIS-STUTTGART, P789

[25] Synthesis of nitrogen heterocycles by intramolecular Michael type of amination via reduction of imines with di-n-butyliodotin hydride (n-Bu2SnIH) [J].

Suwa, T ;

Shibata, I ;

Nishino, K ;

Baba, A .

ORGANIC LETTERS, 1999, 1 (10) :1579-1581

[26]

Suwa T, 2000, SYNLETT, P556

[27] Dehydrogenative silylation of amines and hydrosilylation of imines catalyzed by ytterbium-imine complexes [J].

Takaki, K ;

Kamata, T ;

Miura, Y ;

Shishido, T ;

Takehira, K .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3891-3895

[28]

Tarasevich V.A., 1999, RUSS CHEM REV+, V68, P55, DOI DOI 10.1070/RC1999v068n01ABEH000389

[29] Trimethylsilylcyanation of aldehydes and ketones catalyzed by diorganotin dichlorides [J].

Whitesell, JK ;

Apodaca, R .

TETRAHEDRON LETTERS, 1996, 37 (15) :2525-2528

[30] A convenient synthesis of protected and free homoallylic alcohols: Catalytic use of dibutyltin dichloride in the allylation of aldehydes with allyltributyltin [J].

Whitesell, JK ;

Apodaca, R .

TETRAHEDRON LETTERS, 1996, 37 (23) :3955-3958

← 1 2 3 →