Highly Regioselective Construction of Spirocycles via Phosphine-Catalyzed [3 + 2]-Cycloaddition

Highly Regioselective Construction of Spirocycles via Phosphine-Catalyzed [3 + 2]-Cycloaddition

A direct entry to spirocycles with low to moderate regioselectivity was achieved by triphenylphosphine-catalyzed [3 + 2]-cycloaddition of active ex o-methylenecycles (1) and ethyl 2,3-butadienoate (2). The regioselectivity of the reaction was greatly improved by using the bulky tert-butyl ester of t...

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Veröffentlicht in:Journal of organic chemistry 2002-12, Vol.67 (25), p.8901-8905
Hauptverfasser: Du, Yishu, Lu, Xiyan, Yu, Yihua
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Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
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container_end_page 8905
container_issue 25
container_start_page 8901
container_title Journal of organic chemistry
container_volume 67
creator Du, Yishu
Lu, Xiyan
Yu, Yihua
description A direct entry to spirocycles with low to moderate regioselectivity was achieved by triphenylphosphine-catalyzed [3 + 2]-cycloaddition of active ex o-methylenecycles (1) and ethyl 2,3-butadienoate (2). The regioselectivity of the reaction was greatly improved by using the bulky tert-butyl ester of the 2,3-butadienoate (5). The regioselectivity of the reaction was further enhanced by using the tert-butyl 2-butynoate as the substrate. This protocol provided an efficient entry to the skeleton of spirocarbocycles, especially spiro[4.n]alkanes.
doi_str_mv 10.1021/jo026111t
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subjects Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Chemistry
Exact sciences and technology
Organic chemistry
Preparations and properties
title Highly Regioselective Construction of Spirocycles via Phosphine-Catalyzed [3 + 2]-Cycloaddition
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