Volume 29, Issue 11
Isocyclic Compounds
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ChemInform Abstract: Ti(II)-Mediated Allenyne Cyclization as a New Tool for Generation of Chiral Organotitanium Compounds. Asymmetric Generation of Cyclic Allyltitanium Reagents with No Chiral Auxiliary.

H. URABE

H. URABE

Dep. Biomol. Eng., Tokyo Inst. Technol., Midori, Yokohama 226, Japan

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T. TAKEDA

T. TAKEDA

Dep. Biomol. Eng., Tokyo Inst. Technol., Midori, Yokohama 226, Japan

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D. HIDEURA

D. HIDEURA

Dep. Biomol. Eng., Tokyo Inst. Technol., Midori, Yokohama 226, Japan

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F. SATO

F. SATO

Dep. Biomol. Eng., Tokyo Inst. Technol., Midori, Yokohama 226, Japan

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First published: 23 June 2010

Abstract

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ChemInform Abstract

The cyclization of 1,2-dien-7-ynes, such as (I), and 1,2-dien-6-ynes, such as (V), with Ti complexes generated in situ from Ti(O-iPr)4 and iPr-MgCl leads to 1-alkenyl-2-alkylidenecyclopentanes in moderate to good yields. With chiral (V), the intermediate formation of new chiral titanabicycles allows the stereoselective addition to carbonyl compounds affording optically active substituted cyclopentanes, possible precursors of naturally occurring products.

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