ENANTIOSELECTIVE ORTHO-LITHIATION OF AMINALS OF BENZALDEHYDE CHROMIUMTRICARBONYL COMPLEX

被引：50

作者：

ALEXAKIS, A ^{[1
]}

KANGER, T ^{[1
]}

MANGENEY, P ^{[1
]}

ROSEMUNCH, F ^{[1
]}

PERROTEY, A ^{[1
]}

ROSE, E ^{[1
]}

机构：

[1] UNIV PARIS 06,CNRS,URA 408,CHIM ORGAN LAB,F-75252 PARIS 05,FRANCE

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 01期

关键词：

D O I：

10.1016/0957-4166(94)00348-F

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

The asymmetric ortho lithiation of aminals of benzaldehyde chromiumtricarbonyl complex is described. The best regioisomeric composition is attained with aminal 2d. Quenching with an electrophile and hydrolysis of the aminal back to the aldehyde afford a single enantiomer of the o-substituted benzaldehyde chromiumtricarbonyl complex.

引用

页码：47 / 50

页数：4

共 20 条

[1] REACTIVITY AND DIASTEREOSELECTIVITY OF GRIGNARD-REAGENTS TOWARD THE HYDRAZONE FUNCTIONALITY IN TOLUENE SOLVENT
ALEXAKIS, A
LENSEN, N
TRANCHIER, JP
MANGENEY, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (17) : 4563 - 4565
[2] RESOLUTION AND ASYMMETRIC-SYNTHESIS OF ORTHO-SUBSTITUTED (BENZALDEHYDE)TRICARBONYLCHROMIUM COMPLEXES
ALEXAKIS, A
MANGENEY, P
MAREK, I
ROSEMUNCH, F
ROSE, E
SEMRA, A
ROBERT, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) : 8288 - 8290
[3] ALEXAKIS A, 1993, ORGANIC SYNTHESIS VI, P1
[4] ASYMMETRIC DEPROTONATION AND COMPLEXATION REACTIONS MEDIATED BY CHIRAL KETALS AS A ROUTE TO ORTHO-DISUBSTITUTED (ETA-6-ARENE)CR(CO)3 COMPLEXES
AUBE, J
HEPPERT, JA
MILLIGAN, ML
SMITH, MJ
ZENK, P
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (13) : 3563 - 3570
[5] THE DIASTEREOSELECTIVE FUNCTIONALIZATION OF ARENE TRICARBONYLCHROMIUM COMPLEXES CONTAINING A BENZYLIC HETEROATOM SUBSTITUENT
BLAGG, J
DAVIES, SG
GOODFELLOW, CL
SUTTON, KH
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (08): : 1805 - 1811
[6] TRICARBONYL(1-TRIMETHYLSILYL-2,3-DIMETHOXYBENZENE)-CHROMIUM - A NEW CONFORMATION OF THE TRICARBONYLCHROMIUM ENTITY WITH RESPECT TO A BULKY SUBSTITUENT
BOUTONNET, JC
ROSEMUNCH, F
ROSE, E
JEANNIN, Y
ROBERT, F
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 297 (02) : 185 - 191
[7] STEREOSELECTIVE SYNTHESIS OF HOMOCHIRAL ALPHA SUBSTITUTED ORTHO-METHOXYBENZYL ALCOHOLS VIA NUCLEOPHILIC ADDITIONS TO KINETICALLY RESOLVED HOMOCHIRAL TRICARBONYL (ETA-6-ORTHO-ANISALDEHYDE)CHROMIUM(0)
BROMLEY, LA
DAVIES, SG
GOODFELLOW, CL
[J]. TETRAHEDRON-ASYMMETRY, 1991, 2 (02) : 139 - 156
[8] ASYMMETRIC-SYNTHESIS OF ALPHA-SUBSTITUTED BENZYL ALCOHOLS VIA THE STEREOSELECTIVE ADDITION OF NUCLEOPHILES TO HOMOCHIRAL TRICARBONYL(ETA-6-O-TRIALKYLSILYLBENZALDEHYDE)CHROMIUM(O) COMPLEXES
DAVIES, SG
GOODFELLOW, CL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (02): : 393 - 407
[9] DIASTEREOTOPIC GROUP SELECTIVITY IN THE DEPROTONATION OF (ETA-ARENE)CR(CO)3 COMPLEXES
HEPPERT, JA
THOMASMILLER, ME
MILLIGAN, ML
VANDERVELDE, D
AUBE, J
[J]. ORGANOMETALLICS, 1988, 7 (12) : 2581 - 2584
[10] DIASTEREOTOPIC GROUP-SELECTIVE REACTIONS AT PI-ARENE CHROMIUM DERIVATIVES - DEPROTONATION AND NUCLEOPHILIC-ADDITION REACTIONS OF SUBSTRATES BEARING BENZYLIC CHIRAL CENTERS
HEPPERT, JA
AUBE, J
THOMASMILLER, ME
MILLIGAN, ML
TAKUSAGAWA, F
[J]. ORGANOMETALLICS, 1990, 9 (03) : 727 - 739

← 1 2 →