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

被引：24

作者：

Okamoto, S ^{[1
]}

An, DK ^{[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; elimination; alcohols;

D O I：

10.1016/S0040-4039(98)00829-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of a titanium(II) complex (eta(2)-propene)Ti(O-i-Pr)(2), generated in situ from Ti(O-i-Pr)(4) and 2 equiv of i-PrMgCl, with optically active secondary propargyl phosphate and tertiary propargyl carbonate proceeds with more than 97% chiral transfer, thus providing an efficient and practical method for synthesizing di- and tri-substituted allenyltitaniums with high optical purity. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4551 / 4554

页数：4

共 35 条

[1] Novel addition reactions of titanacycle phosphonates by tuning of Ti(O-i-Pr)4/2i-PrMgCl
Quntar, AA
Srebnik, M
CHEMICAL COMMUNICATIONS, 2003, (01) : 58 - 59
[2] Efficient and practical method for synthesizing optically active indan-2-ols by the Ti(O-i-Pr)4/2 i-PrMgCl-mediated metalative Reppe reaction
Hanazawa, T
Sasaki, K
Takayama, Y
Sato, F
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12): : 4980 - 4983
[3] 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
An, DK
Okamoto, S
Sato, F
TETRAHEDRON LETTERS, 1998, 39 (25) : 4555 - 4558
[4] Efficient one-pot synthesis of 2-substituted furans from 3,3-diethoxypropyne and aldehydes using a Ti(O-i-Pr)4/2i-PrMgCl reagent
Eom, Dcok Ki
Choi, Seong Jib
An, Duk Keun
HETEROCYCLES, 2007, 71 (05) : 1141 - 1146
[5] Intramolecular nucleophilic acyl substitution reaction of 3,4-alkadienyl carbonates mediated by Ti(O-i-Pr)(4)/2 i-PrMgCl reagent. Efficient synthesis of optically active beta,gamma-unsaturated esters with an alpha-substituent
Yoshida, Y
Okamoto, S
Sato, F
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (22): : 7826 - 7831
[6] Synthetic reactions mediated by a Ti(O-i-Pr)4/2 i-PrMgX reagent
Sato, F
Urabe, H
Okamoto, S
SYNLETT, 2000, (06) : 753 - 775
[7] OPTICALLY ACTIVE ISOCYANATES .I. SYNTHESIS OF OPTICALLY ACTIVE N-ALPHA-PHENYLETHYLAMIDES BY REACTION OF ALPHA-PHENYLETHYLISOCYANATE WITH GRIGNARD REAGENT
TERENTEV, AP
GRACHEVA, RA
BEZRUCHK.VT
POLTAVA, OG
JOURNAL OF GENERAL CHEMISTRY USSR, 1967, 37 (07): : 1397 - &
[8] The divalent titanium complex Ti(O-i-Pr)4/2 i-PrMgX as an efficient and practical reagent for fine chemical synthesis
Sato, F
Okamoto, S
ADVANCED SYNTHESIS & CATALYSIS, 2001, 343 (08) : 759 - 784
[9] Efficient and practical method for synthesizing N-heterocyclic compounds using intramolecular nucleophilic acyl substitution reactions mediated by Ti(O-i-Pr)(4)/2i-PrMgX reagent. Synthesis of quinolones, pyrroles, indoles, and optically active N-heterocycles including allopumiliotoxin alkaloid 267A
Okamoto, S
Iwakubo, M
Kobayashi, K
Sato, F
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (30) : 6984 - 6990
[10] Formation of azatitanacyclopentanes from ene-imines and a Ti(O-i-Pr)4/2i-PrMgX reagent and their synthetic reactions
Uchikawa, W
Matsuno, C
Okamoto, S
TETRAHEDRON LETTERS, 2004, 45 (49) : 9037 - 9040

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