Stereoselective oxy-functionalization of γ-silyl allylic alcohols with ozone:: A facile synthesis of silyl peroxide and its reactions

被引：31

作者：

Murakami, Masanori ^{[1
]}

Sakita, Kyohei ^{[1
]}

Igawa, Kazunobu ^{[1
]}

Tomooka, Katsuhiko ^{[1
]}

机构：

[1] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Meguro Ku, Tokyo 1528552, Japan

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 18期

关键词：

D O I：

10.1021/ol061635r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A reaction of gamma-silyl allylic alcohol and its ether with ozone provides synthetically versatile alpha-formyl silyl peroxide in good yield without normal fission of carbon - carbon double bond. Thus, the provided silyl peroxide serves as a good precursor for the stereochemically defined triol derivative via alkylation and reduction of peroxide moiety.

引用

页码：4023 / 4026

页数：4

共 27 条

[1] INTRAMOLECULAR SILYL MIGRATION IN THE SINGLET OXYGENATION OF 2-METHYL-5-TRIMETHYLSILYLFURAN [J].

ADAM, W ;

RODRIGUEZ, A .

TETRAHEDRON LETTERS, 1981, 22 (36) :3505-3508

[2]

[Anonymous], 1982, Ozonation in Organic Chemistry. Volume II: Nonolefinic Compounds

[3] STEREOSELECTIVE TOTAL SYNTHESIS OF (+)-ARTEMISININ, THE ANTIMALARIAL CONSTITUENT OF ARTEMISIA-ANNUA L [J].

AVERY, MA ;

CHONG, WKM ;

JENNINGSWHITE, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (03) :974-979

[4]

Bailey P. S., 1978, OZONATION ORGANIC CH, V1

[5] MECHANISMS OF EPOXIDATION DURING OZONATION OF CARBON-CARBON DOUBLE-BONDS [J].

BAILEY, PS ;

HWANG, HH ;

CHIANG, CY .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (02) :231-234

[6]

BUCHI G, 1978, J AM CHEM SOC, V100, P294

[7]

Castrantas HM, 1965, ASTM STP, V394

[8]

CASTRANTAS HM, 1970, ASTP STP, V471

[9]

CLARK GR, 1985, J ORG CHEM, V50, P1994, DOI 10.1021/jo00211a047

[10] SYNTHESIS OF A CYTOTOXIC VERNOLEPIN PROTOTYPE - OZONIZATION OF SILYLOXYALKENES [J].

CLARK, RD ;

HEATHCOCK, CH .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (08) :1396-1403

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