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Synthesis 2014; 46(19): 2601-2607
DOI: 10.1055/s-0034-1378321
paper
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Construction of Functionalized Cyclopentanes by a Relay Ring-Closing Metathesis and Chiral Amine (Thio)urea-Promoted Michael Addition

Yinan Zhang
Department of Chemistry and Chemical Biology, University of New Mexico, , Albuquerque, NM 87131-0001, USA   Fax: +1(505)2772609   Email: wwang@unm.edu
,
Xixi Song
Department of Chemistry and Chemical Biology, University of New Mexico, , Albuquerque, NM 87131-0001, USA   Fax: +1(505)2772609   Email: wwang@unm.edu
,
Xiaobei Chen
Department of Chemistry and Chemical Biology, University of New Mexico, , Albuquerque, NM 87131-0001, USA   Fax: +1(505)2772609   Email: wwang@unm.edu
,
Aiguo Song
Department of Chemistry and Chemical Biology, University of New Mexico, , Albuquerque, NM 87131-0001, USA   Fax: +1(505)2772609   Email: wwang@unm.edu
,
Shilei Zhang
Department of Chemistry and Chemical Biology, University of New Mexico, , Albuquerque, NM 87131-0001, USA   Fax: +1(505)2772609   Email: wwang@unm.edu
,
Wei Wang*
Department of Chemistry and Chemical Biology, University of New Mexico, , Albuquerque, NM 87131-0001, USA   Fax: +1(505)2772609   Email: wwang@unm.edu
› Author Affiliations
Further Information

Publication History

Received: 06 May 2014

Accepted after revision: 22 May 2014

Publication Date:
24 June 2014 (online)

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Abstract

A relay strategy is described that permits ring-closing metathesis and bifunctional chiral amine (thio)urea-catalyzed Michael­ addition reactions to proceed in a one-pot fashion. The process offers an alternative approach to the synthesis of structurally diverse chiral cyclopentanes in good yields and good enantioselectivities.

Key words

cyclopentanes - organometallics - Michael additions - organocatalysis - ring closure - metathesis
 

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