Concise stereoselective synthesis of 1-perfluoroalkyl enamines via the addition of N-lithiated amines to enol ethers and their subsequent metalation to form new functionalized enamines

被引：22

作者：

Bégué, JP ^{[1
]}

Bonnet-Delpon, D ^{[1
]}

Bouvet, D ^{[1
]}

Rock, MH ^{[1
]}

机构：

[1] Ctr Etud Pharmaceut, CNRS, BioCIS, F-92296 Chatenay Malabry, France

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 11期

关键词：

D O I：

10.1039/a801243a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of lithium amides derived from a range of cyclic, sterically demanding, and chiral amines, to trifluoromethyl (Z)-enol ethers 1 and 4, provides stereoselectively the corresponding (Z)-enamines 3a-e and 7 in good yields. This reaction has been extended to the perfluoroalkyl and chlorofluoroalkyl enol ethers (CF2Cl, C2F5). The enamines can react with (BuLi)-Li-t to give vinylic anions and, after quenching with aldehydes and ethyl chloroformate, provide new functionalized enamines 12-16.

引用

页码：1797 / 1800

页数：4

共 37 条

[1]

Banks R. E., 1979, ORGANOFLUORINE CHEM

[2]

Begue JP, 1996, SYNTHESIS-STUTTGART, P529

[3] DETERMINATION OF Z-CONFIGURATION AND E-CONFIGURATION IN TRIFLUOROMETHYLATED VINYL COMPOUNDS - 3J(CF) COUPLING-CONSTANTS AS A CRITERION FOR CONFIGURATIONAL ASSIGNMENTS [J].

BEGUE, JP ;

BONNETDELPON, D ;

MESUREUR, D ;

OUREVITCH, M .

MAGNETIC RESONANCE IN CHEMISTRY, 1991, 29 (07) :675-678

[4]

BEGUE JP, 1989, SYNTHESIS-STUTTGART, P309

[5] Addition of organolithium reagents to alpha-(trifluoromethyl)styrene: Concise synthesis of functionalised gem-difluoroalkenes [J].

Begue, JP ;

BonnetDelpon, D ;

Rock, MH .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (12) :1409-1413

[6] THE WITTIG REACTION OF PERFLUORO-ACID DERIVATIVES - ACCESS TO FLUORINATED ENOL ETHERS, ENAMINES, AND KETONES [J].

BEGUE, JP ;

BONNETDELPON, D ;

MESUREUR, D ;

NEE, G ;

WU, SW .

JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (14) :3807-3814

[7] Synthesis of hindered and functionalized 1-CF3 substituted olefins via a carbolithiation-elimination-metalation cascade [J].

Begue, JP ;

BonnetDelpon, D ;

Bouvet, D ;

Rock, MH .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9111-9114

[8] FLUORINATED SYNTHONS - REACTIVITY OF 1-R(F)-EPOXY ETHERS WITH LEWIS-ACIDS [J].

BEGUE, JP ;

BENAYOUD, F ;

BONNETDELPON, D .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (16) :5029-5036

[9]

BEGUE JP, 1994, TETRAHEDRON-ASYMMETR, V5, P1094

[10]

Bonnet-Delpon D, 1998, SYNTHESIS-STUTTGART, P288

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