Zirconium-mediated intramolecular ester transfer reaction:: Synthesis of α-substituted γ-aminobutyric acid (GABA) derivatives

被引：15

作者：

Ito, H ^{[1
]}

Omodera, K ^{[1
]}

Takigawa, Y ^{[1
]}

Taguchi, T ^{[1
]}

机构：

[1] Tokyo Univ Pharm & Life Sci, Sch Pharm, Hachioji, Tokyo 1920392, Japan

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 09期

关键词：

D O I：

10.1021/ol025709k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHIC] The zirconium-mediated intramolecular ester transfer reaction of N-alkenyl carbamate derivatives proceeded to give a-substituted gamma-aminobutyric acid (GABA) derivatives in good to excellent yields. Quenching experiments of the reaction mixture with iodine or 02 indicated the presence of a cyclopropane intermediate. The resulting iodide was converted to 2-substituted pyrrolidine-3-carboxylate and/or alpha-alkylidene-gamma-aminobutyric acid derivatives in a stereospecific manner.

引用

页码：1499 / 1501

页数：3

共 19 条

[1]

BLACKBURN TF, 1975, TETRAHEDRON LETT, P3041

[2] CHEMISTRY OF CYCLOPROPANOLS .5. STEREOCHEMISTRY OF ACID- AND BASE-CATALYZED RING OPENING [J].

DEPUY, CH ;

BREITBEI.FW ;

DEBRUIN, KR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (14) :3347-&

[3] HYDROZIRCONATION ORGANIC SYNTHESIS VIA ORGANOZIRCONIUM INTERMEDIATES - SYNTHESIS AND REARRANGEMENT OF ALKYLZIRCONIUM(IV) COMPLEXES AND THEIR REACTION WITH ELECTROPHILES [J].

HART, DW ;

SCHWARTZ, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (26) :8115-8116

[4] HYDROZIRCONATION .3. STEREOSPECIFIC AND REGIOSELECTIVE FUNCTIONALIZATION OF ALKYLACETYLENES VIA VINYLZIRCONIUM(IV) INTERMEDIATES [J].

HART, DW ;

BLACKBURN, TF ;

SCHWARTZ, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (03) :679-680

[5] MITSUNOBU REACTIONS OF N-ALKYL AND N-ACYL SULFONAMIDES - AN EFFICIENT ROUTE TO PROTECTED AMINES [J].

HENRY, JR ;

MARCIN, LR ;

MCINTOSH, MC ;

SCOLA, PM ;

HARRIS, GD ;

WEINREB, SM .

TETRAHEDRON LETTERS, 1989, 30 (42) :5709-5712

[6] INTRAMOLECULAR COCYCLISATION OF CARBONYL GROUPS AND UNACTIVATED ALKENES OR ALKYNES INDUCED BY A LOW-VALENT TITANIUM COMPLEX [J].

HEWLETT, DF ;

WHITBY, RJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (23) :1684-1686

[7] 1,4-Addition reaction of γ,γ-dialkoxyallylic zirconium species as a gem-dialkoxycyclopropyl anion equivalent [J].

Ito, H ;

Sato, A ;

Kusanagi, T ;

Taguchi, T .

TETRAHEDRON LETTERS, 1999, 40 (17) :3397-3398

[8] REDUCTIVE CYCLIZATION OF ENONES BY A TITANIUM CATALYST [J].

KABLAOUI, NM ;

BUCHWALD, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (25) :6785-6786

[9] Titanocene-catalyzed cyclocarbonylation of o-allyl aryl ketones to gamma-butyrolactones [J].

Kablaoui, NM ;

Hicks, FA ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (19) :4424-4431

[10] Diastereoselective synthesis of gamma-butyrolactones from enones mediated or catalyzed by a titanocene complex [J].

Kablaoui, NM ;

Hicks, FA ;

Buchwald, SL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (24) :5818-5819

← 1 2 →