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Synthetic methodologies involving metal-vinylidene species as catalytic intermediates.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Synthetic methodologies involving metal-vinylidene species as catalytic intermediates.
Author:	Rhee, Young Ho.
Description:	649 p.
Notes:	Adviser: Barry M. Trost.
Notes:	Source: Dissertation Abstracts International, Volume: 64-09, Section: B, page: 4359.
Contained By:	Dissertation Abstracts International64-09B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3104132
ISBN:	0496517007

Synthetic methodologies involving metal-vinylidene species as catalytic intermediates.
Rhee, Young Ho.

Synthetic methodologies involving metal-vinylidene species as catalytic intermediates. [electronic resource] - 649 p.

Adviser: Barry M. Trost.

Thesis (Ph.D.)--Stanford University, 2003.

Catalytic reactions involving transition metal-coordinated vinylidene complexes as reactive intermediates have been investigated. Based on the facile formation of ruthenium-oxacarbene complexes from homopropargylic alcohols, a ruthenium-catalyzed oxidative cyclization of homopropargylic alcohols was developed employing N-hydroxysuccinimide as a mild oxidant. Extrapolation of this method to bis-homopropargylic alcohols led to a divergent ruthenium-catalyzed reaction of bis-homopropargylic alcohols that provides a convenient access to either dihydropyrans or valerolactones. This method was applied to a highly flexible approach towards trans-fused polycyclic tetrahydropyrans. The ability to form Rh vinylidene complexes from terminal alkynes was utilized in the development of Rh-catalyzed cycloisomerization of homopropargylic and bis-homopropargylic alcohols. Among the transition metals that perform similar reactions, rhodium catalysts demonstrate the best chemoselectivity and turnover numbers to date.

ISBN: 0496517007Subjects--Topical Terms:

193634
Chemistry, Organic.

Synthetic methodologies involving metal-vinylidene species as catalytic intermediates.
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520 # $a Catalytic reactions involving transition metal-coordinated vinylidene complexes as reactive intermediates have been investigated. Based on the facile formation of ruthenium-oxacarbene complexes from homopropargylic alcohols, a ruthenium-catalyzed oxidative cyclization of homopropargylic alcohols was developed employing N-hydroxysuccinimide as a mild oxidant. Extrapolation of this method to bis-homopropargylic alcohols led to a divergent ruthenium-catalyzed reaction of bis-homopropargylic alcohols that provides a convenient access to either dihydropyrans or valerolactones. This method was applied to a highly flexible approach towards trans-fused polycyclic tetrahydropyrans. The ability to form Rh vinylidene complexes from terminal alkynes was utilized in the development of Rh-catalyzed cycloisomerization of homopropargylic and bis-homopropargylic alcohols. Among the transition metals that perform similar reactions, rhodium catalysts demonstrate the best chemoselectivity and turnover numbers to date.
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