Synthesis of optically active imidazolines, azapenams, dioxocyclams, and bis-dioxocyclams

被引：98

作者：

Hsiao, Y ^{[1
]}

Hegedus, LS ^{[1
]}

机构：

[1] COLORADO STATE UNIV,DEPT CHEM,FT COLLINS,CO 80523

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1997年 / 62卷 / 11期

关键词：

D O I：

10.1021/jo962343e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically active 4-methyl-4-carbomethoxy-Delta(2)-imidazoline was efficiently synthesized on a multigram scale. Photolysis with (methoxymethylcarbene)chromium complex produced the optically active azapenam in good yield and with high stereoselectivity. Acid-catalyzed dimerization followed by reduction produced the corresponding optically active dioxocyclam in good yield. Using a bis-carbene complex, an optically active bis-dioxocyclam was produced in excellent yield.

引用

页码：3586 / 3591

页数：6

共 29 条

[1] ENANTIOSPECIFIC CONVERSION OF (S)-ALANINE TO (R)-ALPHA-METHYL PHENYLALANINE
ALONSO, F
DAVIES, SG
[J]. TETRAHEDRON-ASYMMETRY, 1995, 6 (02) : 353 - 356
[2] Synthesis, resolution, and determination of absolute configuration of a vaulted 2,2'-binaphthol and a vaulted 3,3'-biphenanthrol (VAPOL)
Bao, JM
Wulff, WD
Dominy, JB
Fumo, MJ
Grant, EB
Rob, AC
Whitcomb, MC
Yeung, SM
Ostrander, RL
Rheingold, AL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (14) : 3392 - 3405
[3] SYNTHESIS OF AZAPENAMS, DIAZEPINONES, AND DIOXOCYCLAMS VIA THE PHOTOLYTIC REACTION OF CHROMIUM ALKOXYCARBENE COMPLEXES WITH IMIDAZOLINES
BETSCHART, C
HEGEDUS, LS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) : 5010 - 5017
[4] RECOGNITION OF GUANINE STRUCTURE IN NUCLEIC-ACIDS BY NICKEL-COMPLEXES
BURROWS, CJ
ROKITA, SE
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1994, 27 (10) : 295 - 301
[5] DISTINCTIVE COORDINATION CHEMISTRY AND BIOLOGICAL SIGNIFICANCE OF COMPLEXES WITH MACROCYCLIC LIGANDS
BUSCH, DH
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1978, 11 (10) : 392 - 400
[6] IRON AND COBALT LACUNAR COMPLEXES AS DIOXYGEN CARRIERS
BUSCH, DH
ALCOCK, NW
[J]. CHEMICAL REVIEWS, 1994, 94 (03) : 585 - 623
[7] CRANE CG, 1991, J INORG BIOCHEM, V43, P661
[8] POTENT AND SELECTIVE-INHIBITION OF HUMAN-IMMUNODEFICIENCY-VIRUS (HIV)-1 AND HIV-2 REPLICATION BY A CLASS OF BICYCLAMS INTERACTING WITH A VIRAL UNCOATING EVENT
DECLERCO, E
YAMAMOTO, N
PAUWELS, R
BABA, M
SCHOLS, D
NAKASHIMA, H
BALZARINI, J
DEBYSER, Z
MURRER, BA
SCHWARTZ, D
THORNTON, D
BRIDGER, G
FRICKER, S
HENSON, G
ABRAMS, M
PICKER, D
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1992, 89 (12) : 5286 - 5290
[9] SYNTHESIS OF NONIONIC GADOLINIUM CHELATES USEFUL AS CONTRAST AGENTS FOR MAGNETIC-RESONANCE-IMAGING - 1,4,7-TRIS(CARBOXYMETHYL)-10-SUBSTITUTED-1,4,7,10-TETRAAZACYCLODODECANES AND THEIR CORRESPONDING GADOLINIUM CHELATES
DISCHINO, DD
DELANEY, EJ
EMSWILER, JE
GAUGHAN, GT
PRASAD, JS
SRIVASTAVA, SK
TWEEDLE, MF
[J]. INORGANIC CHEMISTRY, 1991, 30 (06) : 1265 - 1269
[10] ELECTRONIC EFFECTS ON THE STEREOCHEMICAL OUTCOME OF THE PHOTOCHEMICAL-REACTION OF CHROMIUM CARBENE COMPLEXES WITH IMINES TO FORM BETA-LACTAMS
DUMAS, S
HEGEDUS, LS
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (17) : 4967 - 4971

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