ASYMMETRIC NUCLEOPHILIC ACYLATION WITH METALATED AMINO NITRILES - DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED 3-AROYLCYCLOHEXANONES VIA TANDEM MICHAEL ADDITION/ALPHA-ALKYLATION

被引：0

作者：

ENDERS, D

KIRCHHOFF, J

MANNES, D

RAABE, G

机构：

来源：

SYNTHESIS-STUTTGART | 1995年 / 06期

关键词：

ASYMMETRIC SYNTHESIS; AMINO NITRILES; NUCLEOPHILIC ACYLATION; MICHAEL ADDITION; 1,4-DIKETONES;

D O I：

暂无

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tandem conjugate addition/alpha-alkylation of lithiated chiral alpha-amino nitriles 3 and alkyl bromides to 2-cyclohexenone afforded 2-substituted 3-aroylcyclohexanones 5 of high diastereo- and enantiomeric purity (de greater than or equal to 98 %, ee greater than or equal to 97 - greater than or equal to 99 %) and in good overall yields. The absolute configuration of the new stereogenic centres was determined by X-ray structure analysis of the Michael adduct 4c.

引用

页码：659 / 666

页数：8

共 46 条

[1] ASYMMETRIC NUCLEOPHILIC ACYLATION WITH METALATED CHIRAL AMINO NITRILES - ENANTIOSELECTIVE SYNTHESIS OF 1,4-DIKETONES VIA ASYMMETRIC MICHAEL ADDITION
ENDERS, D
MANNES, D
RAABE, G
SYNLETT, 1992, (10) : 837 - 839
[2] Asymmetric nucleophilic α-amino-acylation with metalated chiral amino nitriles:: enantioselective synthesis of 3-substituted 5-amino-4-oxo-esters via asymmetric Michael addition
Enders, D
Shilvock, JP
Raabe, G
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (12): : 1617 - 1619
[3] ASYMMETRIC NUCLEOPHILIC ACYLATION VIA METALATED CHIRAL AMINO CYANIDES - ENANTIOSELECTIVE SYNTHESIS OF 3-SUBSTITUTED 4-OXOESTERS BY ASYMMETRIC MICHAEL ADDITION
ENDERS, D
GERDES, P
KIPPHARDT, H
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1990, 29 (02) : 179 - 181
[4] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF ALPHA-SUBSTITUTED BETA-AMINO ACID-ESTERS BY TANDEM MICHAEL-ADDITION ALPHA-ALKYLATION WITH TMS-SAMP AS CHIRAL EQUIVALENT OF AMMONIA
ENDERS, D
BETTRAY, W
RAABE, G
RUNSINK, J
SYNTHESIS-STUTTGART, 1994, : 1322 - 1326
[5] ASYMMETRIC NUCLEOPHILIC ACYLATION VIA METALATED CHIRAL AMINONITRILES ENANTIOSELECTIVE SYNTHESIS OF ALPHA-HYDROXYKETONES
ENDERS, D
LOTTER, H
MAIGROT, N
MAZALEYRAT, JP
WELVART, Z
NOUVEAU JOURNAL DE CHIMIE-NEW JOURNAL OF CHEMISTRY, 1984, 8 (12): : 747 - 750
[6] ASYMMETRIC NUCLEOPHILIC ACYLATION VIA METALATED ALPHA-AMINO NITRILES POSSESSING AN AXIALLY DISYMMETRIC TERTIARY AMINO GROUP
MAIGROT, N
MAZALEYRAT, JP
WELVART, Z
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (20): : 3916 - 3918
[7] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF TRANS-2-AMINO-CYCLOALKANE-1-CARBOXYLIC ACIDS VIA INTRAMOLECULAR TANDEM MICHAEL-ADDITION ALPHA-ALKYLATION USING TMS-SAMP AS CHIRAL EQUIVALENT OF AMMONIA
ENDERS, D
WIEDEMANN, J
BETTRAY, W
SYNLETT, 1995, (04) : 369 - 371
[8] DIASTEREOSELECTIVE AND ENANTIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED 3-TRIALKYLSTANNYLCYCLOHEXANONES BY MICHAEL ADDITION OF TRIALKYLSTANNYLLITHIUM TO CYCLOHEXENONE SAMP HYDRAZONE
ENDERS, D
HEIDER, KJ
RAABE, G
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (04): : 598 - 600
[9] ENANTIOSELECTIVE SYNTHESIS OF 2-SUBSTITUTED 6-MEMBERED AND 7-MEMBERED LACTONES VIA ALPHA-ALKYLATION OF LACTONE HYDRAZONES
ENDERS, D
GROBNER, R
RUNSINK, J
SYNTHESIS-STUTTGART, 1995, (08): : 947 - 951
[10] Enantioselective synthesis of 2-substituted 5-, 6- and 7-membered lactams via alpha-alkylation of their chiral N-dialkylamino derivatives
Enders, D
Grobner, R
Raabe, G
Runsink, J
SYNTHESIS-STUTTGART, 1996, (08): : 941 - &

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