SYNTHESIS OF OPTICALLY-ACTIVE ARYLGLYCINES BY PHOTOLYSIS OF OPTICALLY-ACTIVE (BETA-HYDROXYAMINO) CARBENE CHROMIUM (0) COMPLEXES

被引：54

作者：

VERNIER, JM ^{[1
]}

HEGEDUS, LS ^{[1
]}

MILLER, DB ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 25期

关键词：

D O I：

10.1021/jo00051a044

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Photolysis of [(amino)(aryl)carbene]chromium complexes having the optically active amino alcohol (1R,2S-(-)- or (1S,2R)-(+)-2-amino-1,2-diphenylethanol as the amino group produced aryl-substituted oxazinones in good yield with reasonable diastereoselectivity. Facile separation of diastereoisomers followed by mild reductive cleavage produced several arylglycines, having either electron-donating or withdrawing groups on the aromatic ring, in good overall yield and with excellent enantiomeric excess.

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页码：6914 / 6920

页数：7

相关论文

共 26 条

[1] TRANSITION METAL CARBENE COMPLEXES .27. RING SUBSTITUTED (METHOXYPHENYCARBENE) - PENTACARBONYLCHROMIUM(O) COMPLEXES [J].

FISCHER, EO ;

KREITER, CG ;

KOLLMEIE.HJ ;

MULLER, J ;

FISCHER, RD .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1971, 28 (02) :237-+

[2] UBERGANGSMETALL-CARBEN-KOMPLEXE .2. PHENYLMETHOXYCARBEN- UND METHYLMETHOXYCARBEN-PENTACARBONYLCHROM -MOLYBDAN -WOLFRAM UND -CYCLOPENTADIENYL-DICARBONYL-MANGAN [J].

FISCHER, EO ;

MAASBOL, A .

CHEMISCHE BERICHTE-RECUEIL, 1967, 100 (07) :2445-&

[3] TRANSITION-METAL CARBENE COMPLEXES .102. PENTACARBONYL(ACYLOXYORGANYLCARBENE) COMPLEXES OF CHROMIUM(0) AND TUNGSTEN(0) [J].

FISCHER, EO ;

SELMAYR, T ;

KREISSL, FR .

CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (08) :2947-2955

[4] Some interconversion reactions of organolithium compounds [J].

Gilman, H ;

Langham, W ;

Moore, FW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1940, 62 :2327-2335

[5] ORGANOMETALLIC PHOTOCHEMISTRY .3. PHOTOLYSIS OF ORTHO ANISYLLITHIUM [J].

GLAZE, WH ;

RANADE, AC .

JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (22) :3331-&

[6] 3-SUBSTITUTED FURANS [J].

GRONOWITZ, S ;

SORLIN, G .

ACTA CHEMICA SCANDINAVICA, 1961, 15 (06) :1419-&

[7] EVIDENCE FOR THE INTERMEDIACY OF CHROMIUM KETENE COMPLEXES IN THE SYNTHESIS OF BETA-LACTAMS BY THE PHOTOLYTIC REACTION OF CHROMIUM CARBENE COMPLEXES WITH IMINES - USE IN AMINO-ACID SYNTHESIS [J].

HEGEDUS, LS ;

DEWECK, G ;

DANDREA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (07) :2122-2126

[8] PHOTOLYTIC REACTIONS OF CHROMIUM AMINOCARBENE COMPLEXES - CONVERSION OF AMIDES TO ALPHA-AMINO-ACIDS [J].

HEGEDUS, LS ;

SCHWINDT, MA ;

DELOMBAERT, S ;

IMWINKELRIED, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (06) :2264-2273

[9] The tertiary oxonium salts, I [J].

Meerwein, H ;

Hinz, G ;

Hofmann, P ;

Kroning, E ;

Pfeil, E .

JOURNAL FUR PRAKTISCHE CHEMIE-LEIPZIG, 1937, 147 (10/12) :257-285

[10]

Meyer E. M., 1985, BIOCATALYSIS ORGANIC, P135