Asymmetric palladium(0) catalyzed tandem alkylation and SN′ cyclization of 1,4-dichlorobut-2-ene by chiral imines of aminoacetonitrile for the total synthesis of 1-aminocyclopropanecarboxylic acids

被引：0

作者：

Dorizon, P ^{[1
]}

Su, GF ^{[1
]}

Ludvig, G ^{[1
]}

Nikitina, L ^{[1
]}

Ollivier, J ^{[1
]}

Salaun, J ^{[1
]}

机构：

[1] Univ Paris Sud, Inst Chim Mol Orsay, CNRS, Lab Carbocycles, F-91405 Orsay, France

来源：

SYNLETT | 1998年 / 05期

关键词：

(-)-and (+)-1-hydroxypinanone aminoacetonitrile imines; E-1-amino-2-vinylcyclopropanecarbonitriles;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral imines (-)- and (+)-8a, prepared from aminoacetonitrile and (-)- or (+)-1-hydroxypinanones, reacted with E- and Z-1,4-dichlorobut-2-enes 1 in the presence of (S)- or (R)-BINAP palladium(0) complexes to produce the diastereoselectively pure 1-amino-2-vinylcyclopropane carbonitrile E-13a, suitable precursor of ACCs. However subsequent Pd(0) induced reversible ring opening of the vinylcyclopropane moiety seems responsible for the low enantiomeric excesses obtained (less than or equal to 32% ee).

引用

页码：483 / +

页数：5

共 12 条

[1] PALLADIUM(0) CATALYZED TANDEM ALKYLATION AND S-N' CYCLIZATION OF 1,4-DICHLOROBUT-2-ENE BY THE N-(DIPHENYLMETHYLENE)ACETONITRILE - A STEREOSELECTIVE SYNTHESIS OF 1-AMINOCYCLOPROPANECARBOXYLIC ACIDS
GAUCHER, A
DORIZON, P
OLLIVIER, J
SALAUN, J
TETRAHEDRON LETTERS, 1995, 36 (17) : 2979 - 2982
[2] Palladium(O) catalyzed tandem alkylation and SN cyclization of 1,4-dichlorobut-2-ene by the N-(diphenylmethylene)acetonitrile. A stereo-selective synthesis of 1-aminocyclopropanecarboxylic acids
Tetrahedron Letters, 36 (17):
[3] Palladium(0) catalyzed tandem alkylation and S-N' cyclization of 1,4-dichlorobut-2-ene. A one pot stereoselective synthesis of highly functionalized cyclopropanes
Franzone, G
Carle, S
Dorizon, P
Ollivier, J
Salaun, J
SYNLETT, 1996, (11) : 1067 - &
[4] New strategies towards asymmetric 1-aminocyclopropanecarboxylic acids: Alkylation and S-N' cyclization of (4S)-1-chloropent-2-en-4-ol derivatives by (N-diphenylmethyleneamino)acetonitrile
Dorizon, P
Ollivier, J
Salaun, J
SYNLETT, 1996, (11) : 1071 - &
[5] Palladium(II)-Catalyzed Asymmetric Tandem Cyclization of 2-Aminoaryl Alkynones: An Approach to Chiral 1,2,3,4-Tetrahydro-β-carbolines
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[6] Highly regioselective synthesis of substituted tetrahydroquinolines by palladium-catalyzed cyclization of substituted 2-amidophenylmalonates with 1,4-diacetoxybut-2-ene
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Maeyama, Yohei
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[7] THE 1ST SYNTHESIS OF CHIRAL PHOSPHINOCARBOXYLIC ACID LIGANDS, TRANS-2-(DIPHENYLPHOSPHINO)CYCLOALKANECARBOXYLIC ACIDS - THE PHOSPHINE-PALLADIUM COMPLEXES CATALYZED ASYMMETRIC ALLYLIC ALKYLATION
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[9] Tandem conjugate addition-aldol cyclization to give optically active 1-Aryl-1H-indenes via asymmetric Pd2+-catalyzed 1,4-addition of arylboronic acids
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Kobayshi, Kenya
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[10] A novel C2-symmetric bisphosphane ligand with a chiral cyclopropane backbone: synthesis and application in the Rh(I)-catalyzed asymmetric 1,4-addition of arylboronic acids
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TETRAHEDRON-ASYMMETRY, 2010, 21 (23) : 2768 - 2774

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