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ChemInform Abstract: The tert-Butanesulfinyl Group: An Ideal Chiral Directing Group and Boc-Surrogate for the Asymmetric Synthesis and Applications of β-Amino Acids.

✍ Scribed by Tony P. Tang; Jonathan A. Ellman

Publisher
John Wiley and Sons
Year
2010
Weight
35 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

The tert-Butanesulfinyl Group: An Ideal Chiral Directing Group and Boc-Surrogate for the Asymmetric Synthesis and Applications of β-Amino Acids.

-The utility of chiral tert-butanesulfinyl imines (I), (III), and (VIII) for the asymmetric synthesis of β-substituted, β,β-and α,β-disubstituted β-amino acids in high yields and diastereoselectivities is demonstrated. The sulfinyl moiety serves also as versatile amine protecting group that is stable to basic conditions and amide bond formations, but can be cleaved by treatment with HCl/EtOH at room temperature, as is exemplified for compound (IIIe). -(TANG,

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