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Synfacts 2007(1): 0049-0049  
DOI: 10.1055/s-2006-955723
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Intermolecular Asymmetric Hydroamination

Contributor(s): Hisashi Yamamoto, Matthew B. Boxer
A. Hu, M. Ogasawara*, T. Sakamoto, A. Okada, K. Nakajima, T. Takahashi*, W. Lin*
University of North Carolina, Chapel Hill, USA; Hokkaido University and Sorst Japan, Sapporo and Aichi University of Education, Japan
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Publication History

Publication Date:
15 December 2006 (online)

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Significance

This report describes the synthesis of 4,4′-di-tert-butyl SEGPHOS (1) and its use and comparison to SEGPHOS as well as BINAP derivatives in the intermolecular hydroamination reaction. The six-step synthesis of the ligand includes a resolution step utilizing DBTA allowing access to both enantiomers of the ligand. The Pd(OTf)2(NCMe)2/1 complex gave the highest ee for the hydroamination of 4-F-styrene with aniline. The 4- and 4′-positions of BINAP are known to be very sensitive for the selectivity of the various asymmetric transformations. This paper describes the similar effect on SEGPHOS ligands.