Synlett 2012; 23(20): 2875-2879
DOI: 10.1055/s-0032-1317478
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© Georg Thieme Verlag Stuttgart · New York

A Perspective on the Stereodefined N,O-Acetals: Synthesis and Potential Applications

Haejin Kim
Department of Chemistry, Pohang University of Science and Technology, Hyoja-dong San 31, Pohang, Kyungbuk, 790-784, Republic of Korea   Fax: +82(54)2793399   Email: yhrhee@postech.ac.kr
,
Young Ho Rhee*
Department of Chemistry, Pohang University of Science and Technology, Hyoja-dong San 31, Pohang, Kyungbuk, 790-784, Republic of Korea   Fax: +82(54)2793399   Email: yhrhee@postech.ac.kr
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Further Information

Publication History

Received: 15 August 2012

Accepted after revision: 21 September 2012

Publication Date:
31 October 2012 (online)


Abstract

Developing chemical reactions that rapidly introduce molecular diversity in a controlled manner represents a prime goal in synthetic organic chemistry. In this regard, our recent studies on the asymmetric synthesis and utilization of stereodefined N,O-acetal opens up a conceptually new methodology. The synthesis of labile N,O-acetals was accomplished by highly efficient and chemoselective Pd-catalyzed asymmetric hydroamination of alkoxyallenes. Furthermore, the utility of the stereodefined N,O-acetals as a stereodiversity-generating element was established by the gold-catalyzed cycloisomerization. In addition to these results, new aspects of the N,O-acetals as diversity-generating elements are also discussed.

 
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