N-tert-Butanesulfinyl Imines: Versatile Intermediates for the Asymmetric Synthesis of Amines
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- 作者：Jonathan A. Ellman ; Timothy D. Owens ; and Tony P. Tang
- 刊名：Accounts of Chemical Research
- 出版年：2002
- 出版时间：November 2002
- 年：2002
- 卷：35
- 期：11
- 页码：984 - 995
- 全文大小：328K
- 年卷期：v.35,no.11(November 2002)
- ISSN：1520-4898
文摘
N-tert-Butanesulfinyl aldimines 3 and ketimines 4 are exceedinglyversatile intermediates for the asymmetric synthesis of amines. TheN-tert-butanesulfinyl imines are prepared in high yields by condensing enantiomerically pure tert-butanesulfinamide 1, which isreadily available in either configuration, with a wide range ofaldehydes and ketones. The tert-butanesulfinyl group activates theimines for the addition of many different classes of nucleophiles,serves as a powerful chiral directing group, and after nucleophilicaddition is readily cleaved by treatment of the product with acid.A wide range of highly enantioenriched amines, including 
rs/alpha.gif" BORDER=0>-branched and rs/alpha.gif" BORDER=0>,rs/alpha.gif" BORDER=0>-dibranched amines, rs/alpha.gif" BORDER=0>- and rs/beta2.gif" BORDER=0 ALIGN="middle">-amino acids, 1,2-and 1,3-amino alcohols, and rs/alpha.gif" BORDER=0>-trifluoromethyl amines, are efficiently synthesized using this methodology. In addition, N-tert-butanesulfinyl imine derivatives provide a new family of ligandsfor asymmetric catalysis.
rs/alpha.gif" BORDER=0>-branched and rs/alpha.gif" BORDER=0>,rs/alpha.gif" BORDER=0>-dibranched amines, rs/alpha.gif" BORDER=0>- and rs/beta2.gif" BORDER=0 ALIGN="middle">-amino acids, 1,2-and 1,3-amino alcohols, and rs/alpha.gif" BORDER=0>-trifluoromethyl amines, are efficiently synthesized using this methodology. In addition, N-tert-butanesulfinyl imine derivatives provide a new family of ligandsfor asymmetric catalysis.