Regioselective formation of 2-alkoxyoxetanes in the photoreaction of aromatic carbonyl compounds with β,β-dimethyl ketene silyl acetals:: notable solvent and silyl group effects

被引：23

作者：

Abe, M ^{[1
]}

Shirodai, Y ^{[1
]}

Nojima, M ^{[1
]}

机构：

[1] Osaka Univ, Fac Engn, Dept Chem Mat, Suita, Osaka 5650871, Japan

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1998年 / 19期

关键词：

D O I：

10.1039/a804521f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Regioselective formation of 2-alkoxyoxetanes 3 was achieved in the photoreactions of aromatic ketones 2 with electron-rich ketene silyl acetals 1. In the photoreactions, the silyl-migration adduct 5 was also formed together with the oxetane 3. The product ratios of 3 and 5 were largely dependent on the solvent used and the silyl group of 1. The exclusive formation of 2-alkoxyoxetanes 3 was controlled by proper choice of the solvent and silyl group.

引用

页码：3253 / 3260

页数：8

共 39 条

[1] Regio- and stereo-selective formation of 2-siloxy-2-alkoxyoxetanes in the photoreaction of cyclic ketene silyl acetals with 2-naphthaldehyde and their transformation to aldol-type adducts [J].

Abe, M ;

Ikeda, M ;

Shirodai, Y ;

Nojima, M .

TETRAHEDRON LETTERS, 1996, 37 (33) :5901-5904

[2] STEREOCHEMISTRY AND REGIOCHEMISTRY OF ALDEHYDE INSERTIONS INTO THE C-SI BONDS OF SILIRANES [J].

BODNAR, PM ;

PALMER, WS ;

SHAW, JT ;

SMITROVICH, JH ;

SONNENBERG, JD ;

PRESLEY, AL ;

WOERPEL, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (42) :10575-10576

[3]

Carless H. A. J., 1984, SYNTHETIC ORGANIC PH, P425

[4] PHOTOCHEMICAL SYNTHESES OF 2,6-DIOXABICYCLO[3.2.0]HEPTANES [J].

CARLESS, HAJ ;

HAYWOOD, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1980, (22) :1067-1068

[5]

CARLESS HAJ, 1995, ORGANIC PHOTOBIOLOGY, P560

[6] Chemistry of trichlorosilyl enolates .1. New reagents for catalytic, asymmetric aldol additions [J].

Denmark, SE ;

Winter, SBD ;

Su, XP ;

Wong, KT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (31) :7404-7405

[7] NUCLEOPHILE-ASSISTED CLEAVAGE OF SILANE CATION RADICALS [J].

DINNOCENZO, JP ;

FARID, S ;

GOODMAN, JL ;

GOULD, IR ;

TODD, WP ;

MATTES, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8973-8975

[8] Nucleophile-assisted cleavage of benzyltrialkylsilane cation radicals [J].

Dockery, KP ;

Dinnocenzo, JP ;

Farid, S ;

Goodman, JL ;

Gould, IR ;

Todd, WP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (08) :1876-1883

[9] ELECTRON-TRANSFER OXIDATION OF KETENE SILYL ACETALS AND OTHER ORGANOSILANES - THE MECHANISTIC INSIGHT INTO LEWIS ACID MEDIATED ELECTRON-TRANSFER [J].

FUKUZUMI, S ;

FUJITA, M ;

OTERA, J ;

FUJITA, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10271-10278

[10] ADDITION OF ORGANOSILANES WITH AROMATIC CARBONYL-COMPOUNDS VIA PHOTOINDUCED ELECTRON-TRANSFER IN THE PRESENCE OF MAGNESIUM PERCHLORATE [J].

FUKUZUMI, S ;

OKAMOTO, T ;

OTERA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) :5503-5504

← 1 2 3 4 →