Asymmetric cyclopropanation of chiral (1-dimethoxyphosphoryl-2-phenyl)vinyl p-tolyl sulfoxide:: a new synthesis of enantiomerically pure 2-amino-3-phenyl-1-cyclopropane-phosphonic acid -: a constrained analog of phaclofen

被引：35

作者：

Midura, WH ^{[1
]}

Mikolajczyk, M ^{[1
]}

机构：

[1] Polish Acad Sci, Ctr Mol & Macromol Studies, Dept Heteroorgan Chem, PL-90363 Lodz, Poland

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 16期

关键词：

asymmetric cyclopropanation; chiral alpha-phosphorylvinyl sulfoxides aminocyclopropanephosphonic acid;

D O I：

10.1016/S0040-4039(02)00374-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

E-(S)-(1-Dimethoxyphosphoryl-2-phenyl)vinyl p-tolyl sulfoxide 3 was found to undergo cyclopropanation with sulfur ylides [dimethyl(oxo)sulfonium methylide, diphenyl sulfonium isopropylide and ethyl (dimethylsulfuranylidene)acetate (EDSA)] in a highly diastereoselective manner. The major diastereomer obtained in the reaction of E-(S)-3 with EDSA vas converted into enantiopure (2R)-amino-(3R)-phenyl-(1R)-cyclopropane-phosphonic acid, a constrained analog of the GABA(B) antagonist. phaclofen. (C) 2002 Published by Elsevier Science Ltd.

引用

页码：3061 / 3065

页数：5

共 29 条

[21] Electroluminescence spikes of pulsed organic light-emitting diodes at switch-off using 1,4-bis[2-[4-[N,N-di(p-tolyl)amino]phenyl]vinyl]benzene as a light-emitting layer
Wei, Bin
Horiba, Yashuhiro
Furukawa, Kenji
Ichikawa, Musubu
Koyama, Toshiki
Taniguchi, Yoshio
Japanese Journal of Applied Physics, Part 1: Regular Papers and Short Notes and Review Papers, 2005, 44 (6 A): : 4248 - 4251
[22] A NEW ASYMMETRIC-SYNTHESIS OF (R)-3-ARYLPHTHALIDES AND (S)-3-ARYLPHTHALIDES - EXTREMELY HIGH DIASTEREOSELECTIVE REACTION OF ARYLCARBALDEHYDES WITH CHIRAL [2-(1,3-OXAZOLIDIN-2-YL)PHENYL]TITANIUM ATE COMPLEXES
TAKAHASHI, H
TSUBUKI, T
HIGASHIYAMA, K
SYNTHESIS-STUTTGART, 1992, (07): : 681 - 684
[23] Synthesis of enantiomerically pure beta-amino acids from 2-tert-butyl-1-carbomethoxy-2,3-dihydro-4(1H)-pyrimidinone: (R)-3-amino-3-(p-methoxyphenyl)propionic acid - (1(2H)-pyrimidinecarboxylic acid, 2-(1,1-dimethylethyl)-3,4-dihydro-4-oxo, methyl ester, (R)- or (S)-)
Lakner, FJ
Chu, KS
Negrete, GR
Konopelski, JP
ORGANIC SYNTHESIS, VOL 73, 1996, 73 : 201 - 214
[24] Design, synthesis and anti-tubercular evaluation of new 2-acylated and 2-alkylated amino-5-(4-(benzyloxy)phenyl)thiophene-3-carboxylic acid derivatives. Part 1
Lu, Xiaoyun
Wan, Baojie
Franzblau, Scott G.
You, Qidong
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) : 3551 - 3563
[25] STUDIES IN ANTIFERTILITY AGENTS .15. SYNTHESIS OF 1,2-TRANS-7-HYDROXY-1,2,3,4,9,10-HEXAHYDROPHENANTHRENE-2-CARBOXYLIC ACID, 1,10A-TRANS-1-[P-(OMEGA-T-AMINOALKOXY)PHENYL] AND 1,10A-TRANS-7-[P-(OMEGA-T-AMINO)ALKOXY]-1-PHENYL-1,2,3,9,10,10A-HEXAHYDROPHENANTHRENES AND 1,10A-TRANS-(B-C-CIS AND B-C-TRANS)-1,2,3,4,4A,9,10,10A-OCTAHYDRO-1-PHENYLPHENANTHRENESR
ANANTHANARAYANAN, CV
ANAND, N
BINDRA, JS
NEYYARAPALLY, AT
RASTOGI, SN
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1977, 15 (02): : 154 - 162
[26] Synthesis, antimicrobial, insecticidal and anthelmintic activity studies of some new alkyl/aryl 6-(4-(4-(4-methyl-1H-1,2,3-triazol-1-yl)phenyl amino)phenyl)-N2,N4-bis(4-methoxyphenyl)-1,3,5-triazin-2,4-diamine carbamic acid ester derivatives
Gautam, Nidhi
Chourasia, O. P.
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2012, 51 (07): : 1020 - 1026
[27] ANALOGS OF TETRAHYDROFOLIC ACID .9. SYNTHESIS OF N-[1-(2-AMINO-4-HYDROXY-6-PHENYL-5-PYRIMIDYL)-3-PROPYL]-P-AMINOBENZOYL-L-GLUTAMIC ACID, A NONCLASSICAL INHIBITOR OF SOME FOLIC COFACTOR AREA ENZYMES
BAKER, BR
SHAPIRO, HS
JOURNAL OF MEDICINAL CHEMISTRY, 1963, 6 (06) : 664 - &
[28] SYNTHESIS OF AN OPTICALLY-ACTIVE PLATINUM(II) COMPLEX CONTAINING A NEW TERDENTATE P-C-P LIGAND AND ITS CATALYTIC ACTIVITY IN THE ASYMMETRIC ALDOL REACTION OF METHYL ISOCYANOACETATE - X-RAY CRYSTAL-STRUCTURE OF [2,6-BIS[1'S,2'S)-1'-(DIPHENYLPHOSPHINO)-2',3'-O-ISOPROPYLIDENE-2',3'-DIHYDROXYPROPYL[PHENYL](ETA'-NITRATO)PLATINUM(II)
GORLA, F
TOGNI, A
VENANZI, LM
ALBINATI, A
LIANZA, F
ORGANOMETALLICS, 1994, 13 (05) : 1607 - 1616
[29] A new family of chiral chelating diamines with transition-metal stereocenters:: Synthesis, structure, and reactivity of the enantiomerically pure dirhenium-substituted 1,2-diamine (η5-C5H5)Re(NO)(PPh3) (CH2N(CH3)CH2CH2(H3C)NCH2)(Ph3P)(ON)Re(η5-C5H5)
Alvey, LJ
Delacroix, O
Wallner, C
Meyer, O
Hampel, F
Szafert, S
Lis, T
Gladysz, JA
ORGANOMETALLICS, 2001, 20 (14) : 3087 - 3096

← 1 2 3 →