Catalytic Asymmetric Mannich-Type Reaction of N-Alkylidene-α-Aminoacetonitrile with Ketimines

被引：48

作者：

Lin, Shaoquan ^{[1
]}

Kawato, Yuji ^{[1
]}

Kumagai, Naoya ^{[1
]}

Shibasaki, Masakatsu ^{[1
,2
]}

机构：

[1] Inst Microbial Chem BIKAKEN, Shinagawa Ku, Tokyo 1410021, Japan

[2] ACT C, JST, Shinagawa Ku, Tokyo 1410021, Japan

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2015年 / 54卷 / 17期

关键词：

asymmetric catalysis; copper; ketimines; Mannich reaction; nitriles; METALATED AZOMETHINE YLIDES; PHASE-TRANSFER CATALYSIS; AMINO-ACID-ESTERS; 1-AMINOCYCLOPROPANECARBOXYLIC ACIDS; ALPHA; BETA-UNSATURATED ESTERS; STEREOSELECTIVE-SYNTHESIS; ORGANIC-SYNTHESIS; PRACTICAL METHOD; SCHIFF-BASES; ALKYLATION;

D O I：

10.1002/anie.201412377

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Optically active vicinal diamines are versatile chiral building blocks in organic synthesis. A soft Lewis acid/hard Bronsted base cooperative catalyst allows for an efficient stereoselective coupling of N-alkylidene-alpha-aminoacetonitrile and ketimines to access this class of compounds bearing consecutive tetra-and trisubstituted stereogenic centers. The strategic use of a soft Lewis basic thiophosphinoyl group for ketimines is the key to promoting the reaction, and aliphatic ketimines serve as suitable substrates with as little as 3 mol% catalyst loading.

引用

页码：5183 / 5186

页数：4

共 70 条

[1] REACTIONS OF ACYL ANION EQUIVALENTS DERIVED FROM CYANOHYDRINS, PROTECTED CYANOHYDRINS AND ALPHA-DIALKYLAMINONITRILES [J].

ALBRIGHT, JD .

TETRAHEDRON, 1983, 39 (20) :3207-3233

[2]

Arseniyadis S., 1984, Org. React, V31, P1, DOI DOI 10.1002/0471264180.OR031.01

[3] THE FATE OF VALINE-OXYGEN DURING PENICILLIN BIOSYNTHESIS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

BIRD, JW ;

SCHOFIELD, CJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (21) :1615-1616

[4] CEPHALOSPORIN BIOSYNTHESIS - A BRANCHED PATHWAY SENSITIVE TO AN ISOTOPE EFFECT [J].

BALDWIN, JE ;

ADLINGTON, RM ;

CROUCH, NP ;

SCHOFIELD, CJ ;

TURNER, NJ ;

APLIN, RT .

TETRAHEDRON, 1991, 47 (47) :9881-9900

[5] Synthesis of γ-amino acid esters by 1,4-addition of deprotonated α-aminonitriles and α-(alkylideneamino)nitriles to α,β-unsaturated esters [J].

Bergner, Ines ;

Opatz, Till .

SYNTHESIS-STUTTGART, 2007, (06) :918-928

[6] Catalytic Carbon-Carbon Bond-Forming Reactions of Aminoalkane Derivatives with Imines [J].

Chen, Yi-Jing ;

Seki, Kazutaka ;

Yamashita, Yasuhiro ;

Kobayashi, Shu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (10) :3244-+

[7]

Chengzhi Cai, 1994, Tetrahedron, V50, P5735, DOI 10.1016/S0040-4020(01)85641-6

[8]

Dorizon P, 1996, SYNLETT, P1071

[9] Stereoselective synthesis of highly functionalized cyclopropanes.: Application to the asymmetric synthesis of (1S,2S)-2,3-methanoamino acids [J].

Dorizon, P ;

Su, GF ;

Ludvig, G ;

Nikitina, L ;

Paugam, R ;

Ollivier, J ;

Salaün, J .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (13) :4712-4724

[10] PHASE-TRANSFER CATALYZED ADDITIONS .6. REACTION OF N-DIPHENYLMETHYLENEAMINOACETONITRILE WITH AROMATIC-ALDEHYDES [J].

DRYANSKA, V .

SYNTHETIC COMMUNICATIONS, 1990, 20 (07) :1055-1061

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