4.7 Article

Bench-stable imine surrogates for the one-pot and catalytic asymmetric synthesis of α-amino esters/ketones

Journal

CHEMICAL COMMUNICATIONS
Volume 56, Issue 91, Pages 14243-14246

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d0cc06055k

Keywords

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Funding

  1. Ministry of Science and Technology of China [2019ZX09301-164]
  2. Natural Science Foundation of Chongqing, China [cstc2019jcyj-zdxmX0021]

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N,O-Bis(tert-butoxycarbonyl)hydroxylamines are readily accessible as imine surrogates, which are bench stable and could quantitatively generate the corresponding imines for in situ applications. An unpresented catalytic asymmetric method for the synthesis of alpha-amino esters and ketones from novel imine surrogates, N,O-bis(tert-butoxycarbonyl)hydroxylamines, as well as its preliminary mechanistic studies are reported. A variety of optically enriched products were obtained in excellent yields and enantioselectivities (up to 99% yield and >99% ee).

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