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Synlett 2012; 23(20): 2875-2879
DOI: 10.1055/s-0032-1317478
DOI: 10.1055/s-0032-1317478
synpacts
A Perspective on the Stereodefined N,O-Acetals: Synthesis and Potential Applications
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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For selected examples on the use of nonallylic N,O-acetals as iminium ion precursors, see:
For selected examples for the nonstereoselective synthesis of N,O-acetals, see:
For the synthesis and utility of nonstereodefined allylic N,O-acetals, see:
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