Stereodivergent synthesis of enantiopure cis- and trans-3-ethyl-4-piperidineacetates

被引：39

作者：

Amat, M ^{[1
]}

Pérez, M ^{[1
]}

Llor, N ^{[1
]}

Bosch, J ^{[1
]}

机构：

[1] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 16期

关键词：

D O I：

10.1021/ol0263245

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Starting from a common chiral bicyclic lactam 11, enantiopure trans- or cis-3-ethyl-4-piperidineacetate derivatives are obtained by conjugate addition of an enolate or a cuprate to the unsaturated lactams 12 or 18, respectively.

引用

页码：2787 / 2790

页数：4

共 24 条

[1] Amat M, 2002, ANGEW CHEM INT EDIT, V41, P335, DOI 10.1002/1521-3773(20020118)41:2<335::AID-ANIE335>3.0.CO
[2] 2-Y
[3] Conjugate addition of organocuprates to chiral bicyclic δ-lactams.: Enantioselective synthesis of cis-3,4-disubstituted and 3,4,5-trisubstituted piperidines
Amat, M
Pérez, M
Llor, N
Bosch, J
Lago, E
Molins, E
[J]. ORGANIC LETTERS, 2001, 3 (04) : 611 - 614
[4] Synthesis of enantiopure trans-3,4-disubstituted piperidines.: An enantiodivergent synthesis of (+)- and (-)-paroxetine
Amat, M
Bosch, J
Hidalgo, J
Cantó, M
Pérez, M
Llor, N
Molins, E
Miravitlles, C
Orozco, M
Luque, J
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10) : 3074 - 3084
[5] IPECACUANHA ALKALOIDS .5. STEREOSPECIFIC SYNTHESIS OF (+)-O-METHYLPSYCHOTRINE AND (-)-EMETINE
BATTERSBY, AR
TURNER, JC
[J]. JOURNAL OF THE CHEMICAL SOCIETY, 1960, (FEB): : 717 - 725
[6] BROWN RT, 1978, TETRAHEDRON LETT, P1605
[7] BROWN RT, 1983, CHEM HETEROCYCLIC 4, V25, pCH3
[8] STEREOCHEMISTRY OF CONJUGATE ADDITION TO 4-SUBSTITUTED AND 5-SUBSTITUTED ALPHA,BETA-UNSATURATED DELTA-LACTONES
FLEMING, I
REDDY, NL
TAKAKI, K
WARE, AC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (19) : 1472 - 1474
[9] Racemic and chiral syntheses of some indolo[2,3-a]quinolizidine alkaloids through a "lactim ether route"
Fujii, T
Ohba, M
[J]. HETEROCYCLES, 1998, 47 (01) : 525 - 539
[10] CHIRAL SYNTHESES OF BENZO[A]QUINOLIZIDINE-TYPE ALANGIUM ALKALOIDS
FUJII, T
OHBA, M
YOSHIFUJI, S
[J]. HETEROCYCLES, 1988, 27 (04) : 1009 - 1033

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