A Diversity-Oriented Approach to Spirocyclic and Fused Hydantoins via Olefin Metathesis

Dhara, Kalyan ; Midya, Ganesh Chandra ; Dash, Jyotirmayee (2012) A Diversity-Oriented Approach to Spirocyclic and Fused Hydantoins via Olefin Metathesis Journal of Organic Chemistry, 77 (18). pp. 8071-8082. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/jo301234r

Related URL: http://dx.doi.org/10.1021/jo301234r

Abstract

An efficient and general method is reported to prepare a diverse series of 5,5-spirocyclic and 1,5-, 4,5-, and 3,4-fused bicyclic imidazolidinone derivatives based on selective alkylation and ring closing metathesis (RCM) by exploiting the four possible points of diversity in the hydantoin ring. Hydantoins containing trienes and tetraenes undergo selective RCM and cross metathesis to afford functionalized spirohydantoins. A tandem metathesis sequence involving ring closing-ring opening-ring closing and cross metathesis (RC-RO-RC-CM) occurred with a hydantoin triene to give a bicyclic hydantoin dimer in high yield. The fused bicylic dimer could participate in cross metathesis to produce a functionalized fused hydantoin derivative. The methodology establishes novel routes to unnatural amino acids, proline homologues, and cyclic vicinal diamines.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:126567
Deposited On:17 Oct 2022 05:49
Last Modified:17 Oct 2022 05:49

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