Organocatalytic Enantioselective Cascade Michael–Aldol Condensation Reactions: Efficient Assembly of Densely Functionalized Chiral Cyclopentenes†
Jian Wang Dr.
Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001, USA, Fax: (+1) 505-277-2609
Search for more papers by this authorHao Li
Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001, USA, Fax: (+1) 505-277-2609
Search for more papers by this authorHexin Xie
Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001, USA, Fax: (+1) 505-277-2609
Search for more papers by this authorLiansuo Zu
Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001, USA, Fax: (+1) 505-277-2609
Search for more papers by this authorXu Shen Prof. Dr.
Department of Pharmacology, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
School of Pharmacy, East China University of Science & Technology, Shanghai 200237, China
Search for more papers by this authorWei Wang Prof. Dr.
Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001, USA, Fax: (+1) 505-277-2609
Department of Pharmacology, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
Search for more papers by this authorJian Wang Dr.
Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001, USA, Fax: (+1) 505-277-2609
Search for more papers by this authorHao Li
Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001, USA, Fax: (+1) 505-277-2609
Search for more papers by this authorHexin Xie
Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001, USA, Fax: (+1) 505-277-2609
Search for more papers by this authorLiansuo Zu
Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001, USA, Fax: (+1) 505-277-2609
Search for more papers by this authorXu Shen Prof. Dr.
Department of Pharmacology, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
School of Pharmacy, East China University of Science & Technology, Shanghai 200237, China
Search for more papers by this authorWei Wang Prof. Dr.
Department of Chemistry & Chemical Biology, University of New Mexico, MSC03 2060, Albuquerque, NM 87131-0001, USA, Fax: (+1) 505-277-2609
Department of Pharmacology, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
Search for more papers by this authorFinancial support of this research by the University of New Mexico, ACS-PRF, NSF (CHE 0704015), and NIH-INBRE program (P20 RR016480) is gratefully acknowledged. Thanks are expressed to Dr. Elieen N. Duesler for performing X-ray analysis.
Graphical Abstract
A cascade of possibility: A novel and highly enantioselective cascade Michael–aldol condensation reaction of α,β-unsaturated aldehydes with dimethyl malonate aldehyde has been developed. The process, efficiently catalyzed by a simple chiral diphenylprolinol TES ether, serves as a powerful approach to the preparation of highly functionalized chiral cyclopentenes with the formation of two new CC bonds. TES=triethylsilyl.
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2007/z703163_s.pdf or from the author.
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