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Unusual Domino Michael/Aldol Condensation Reactions Employing Oximes as N-Selective Nucleophiles: Synthesis of N-Hydroxypyrroles

Authors

  • Bin Tan,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
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  • Zugui Shi,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
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  • Pei Juan Chua,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
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  • Yongxin Li Dr.,

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
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  • Guofu Zhong Prof. Dr.

    1. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371 (Singapore), Fax: (+65) 6791-1961
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  • Research support from the Ministry of Education in Singapore (ARC12/07 #T206B3225) and Nanyang Technological University (URC RG53/07 and SEP RG140/06) is gratefully acknowledged. We are very grateful to Prof. K. Narasaka and Dr. S. Chiba for helpful discussions.

Abstract

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A facile synthesis of N-hydroxypyrroles has been developed using readily available α-carbonyl oximes and α,β-unsaturated aldehydes. The domino reaction proceeds through iminium activation of α,β-unsaturated aldehydes, Michael addition using oximes as N-selective nucleophiles, and aldol condensation.

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