Synthesis of chiral alkynes having 2H or halogen at the secondary or tertiary propargylic stereogenic center by hydrolysis and halogenolysis of optically active allenyltitaniums having axial chirality

被引：18

作者：

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 / 25期

关键词：

titanium and compounds; asymmetric synthesis; alkynes; halogens and compounds;

D O I：

10.1016/S0040-4039(98)00830-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The hydrolysis and halogenolysis of optically active allenyltitaniums, generated by the reaction of a Ti(O-i-Pr)(4) /2 i-PrMgCl reagent with optically active propargyl alcohol derivatives, proceed in a regioselective way and with excellent degree of chiral transfer, thus opening up a highly efficient and practical route to chiral alkynes having H-2 or Cl at the stereogenic propargylic center, (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4555 / 4558

页数：4

共 20 条

[11] Dynamic kinetic protonation of racemic allenylmetal species for the asymmetric synthesis of allenic esters [J].

Mikami, K ;

Yoshida, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (08) :858-860

[12] CHIRAL [H-2]-LABELED METHYLENE GROUPS IN TRIENOIC FATTY AND DIENOIC FATTY-ACIDS - A FACILE APPROACH VIA ASYMMETRIC EPOXIDATION OF [H-2]ALLYL ALCOHOLS [J].

NEUMANN, C ;

BOLAND, W .

HELVETICA CHIMICA ACTA, 1990, 73 (03) :754-761

[13]

Norley M, 1996, SYNLETT, P900

[14] Synthesis of optically active allenyltitaniums having axial chirality by the reaction of optically active propargylic compounds with a Ti(O-i-Pr)4/2i-PrMgCl reagent [J].

Okamoto, S ;

An, DK ;

Sato, F .

TETRAHEDRON LETTERS, 1998, 39 (25) :4551-4554

[15]

OVERMAN LE, 1988, J CHEM SOC P1, P85

[16]

Reetz M. T., 1986, ORGANOTITANIUM REAGE

[17] Enantioselective total synthesis of fumonisin B-2 [J].

Shi, Y ;

Peng, LF ;

Kishi, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (17) :5666-5667

[18]

SIMO MS, 1972, ORGANOMETAL CHEM, V35, pC23

[19]

Yamamoto H., 1991, COMPREHENSIVE ORGANI, V2, P81, DOI [10.1016/B978-0-08052349-1.00025-1, DOI 10.1016/B978-0-08052349-1.00025-1]

[20]

YAMAMOTO Y, 1984, J CHEM SOC CHEM COMM, P1004, DOI 10.1039/c39840001004

← 1 2 →