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
Abe, M
Ikeda, M
Shirodai, Y
Nojima, M
[J]. TETRAHEDRON LETTERS, 1996, 37 (33) : 5901 - 5904
[2] STEREOCHEMISTRY AND REGIOCHEMISTRY OF ALDEHYDE INSERTIONS INTO THE C-SI BONDS OF SILIRANES
BODNAR, PM
PALMER, WS
SHAW, JT
SMITROVICH, JH
SONNENBERG, JD
PRESLEY, AL
WOERPEL, KA
[J]. 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
CARLESS, HAJ
HAYWOOD, DJ
[J]. 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
Denmark, SE
Winter, SBD
Su, XP
Wong, KT
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (31) : 7404 - 7405
[7] NUCLEOPHILE-ASSISTED CLEAVAGE OF SILANE CATION RADICALS
DINNOCENZO, JP
FARID, S
GOODMAN, JL
GOULD, IR
TODD, WP
MATTES, SL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) : 8973 - 8975
[8] Nucleophile-assisted cleavage of benzyltrialkylsilane cation radicals
Dockery, KP
Dinnocenzo, JP
Farid, S
Goodman, JL
Gould, IR
Todd, WP
[J]. 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
FUKUZUMI, S
FUJITA, M
OTERA, J
FUJITA, Y
[J]. 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
FUKUZUMI, S
OKAMOTO, T
OTERA, J
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (12) : 5503 - 5504

← 1 2 3 4 →