An efficient method for conversion of 1-alken-3-yl carbonates to 1-alkenes and 3-chloro-1-alkenes via allyltitaniums

被引：12

作者：

Matsuda, S ^{[1
]}

An, DK ^{[1
]}

Okamoto, S ^{[1
]}

Sato, F ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Biomol Engn, Midori Ku, Yokohama, Kanagawa 2268501, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 41期

关键词：

titanium and compounds; alkenes; halogens and compounds; steroids and sterols;

D O I：

10.1016/S0040-4039(98)01633-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Hydrolysis and halogenolysis of the allyltitaniums derived from allylic carbonates and a Ti(O-i-Pr)(4) / 2 i-PrMgCl reagent proceed with high regio- and stereoselectivity, thus providing an efficient method for converting 1-alken-3-yl carbonates to l-alkenes or 3-chloro-1-alkenes. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：7513 / 7516

页数：4

共 19 条

[1] ISOLATION OF THE MURICINS - EVIDENCE OF A CHEMICAL ADAPTATION AGAINST FOULING IN THE MARINE OCTOCORAL MURICEA-FRUTICOSA (GORGONACEA) [J].

BANDURRAGA, MM ;

FENICAL, W .

TETRAHEDRON, 1985, 41 (06) :1057-1065

[2] KINETICS OF THE PROTODESTANNYLATION OF ALLENYLTINS [J].

COCHRAN, JC ;

KUIVILA, HG .

ORGANOMETALLICS, 1982, 1 (01) :97-103

[3] AN IMPROVED ROUTE TO PREGNA-5,20-DIEN-3-BETA-OL (MURICIN AGLYCONE) - CARBON AND PROTON NUCLEAR-MAGNETIC-RESONANCE ASSIGNMENTS FOR THE AGLYCONE AND A NUMBER OF RELATED PREGNENE DERIVATIVES [J].

DAWE, RD ;

WRIGHT, JLC .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1987, 65 (03) :666-669

[4]

GAO Y, 1995, ORG CHEM, V60, P8136

[5]

HALPERT J, 1988, MOL PHARMACOL, V34, P148

[6] Efficient synthesis of 7-, 8- and 9-membered cyclic allyltitanium compounds and their stereoselective addition reaction with aldehydes and imines [J].

Hikichi, S ;

Gao, Y ;

Sato, F .

TETRAHEDRON LETTERS, 1997, 38 (16) :2867-2870

[7] PREPARATION AND REGIOSELECTIVE AND DIASTEREOSELECTIVE REACTIONS OF ALLYLIC ZIRCONIUM REAGENTS FROM ALLYLIC ETHER DERIVATIVES [J].

ITO, H ;

TAGUCHI, T ;

HANZAWA, Y .

TETRAHEDRON LETTERS, 1992, 33 (10) :1295-1298

[8] Unusual regioselectivity in the reaction of allyl- or allenylpropargyltitanium compounds with carbonyl compounds: An efficient synthesis of alkylidenecyclopropane derivatives [J].

Kasatkin, A ;

Sato, F .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1996, 35 (23-24) :2848-2849

[9] NEW, EFFICIENT METHOD FOR THE SYNTHESIS OF ALLYLTITANIUM COMPOUNDS FROM ALLYL HALIDES OR ALLYL ALCOHOL DERIVATIVES VIA OXIDATIVE ADDITION - A HIGHLY EFFICIENT AND PRACTICAL SYNTHESIS OF HOMOALLYL ALCOHOLS [J].

KASATKIN, A ;

NAKAGAWA, T ;

OKAMOTO, S ;

SATO, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (13) :3881-3882

[10] NOVEL METHOD FOR STEREOSPECIFIC GENERATION OF NATURAL C-17 STEREOCHEMISTRY AND EITHER C-20 EPIMER IN STEROID SIDE-CHAINS BY PALLADIUM-CATALYZED HYDROGENOLYSIS OF C-17 AND C-20 ALLYLIC CARBONATES [J].

MANDAI, T ;

MATSUMOTO, T ;

KAWADA, M ;

TSUJI, J .

TETRAHEDRON, 1994, 50 (02) :475-486

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