4.8 Article

A Highly Stereoselective Organocatalytic Tandem Aminoxylation/Aza-Michael Reaction for the Synthesis of Tetrahydro-1,2-Oxazines

Journal

ORGANIC LETTERS
Volume 10, Issue 20, Pages 4585-4588

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol801864c

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Funding

  1. Ministry of Education in Singapore [ARC12/07, T206133225]
  2. Nanyang Technological University [RG53/07, RG140/06]

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A facile stereoselective synthesis of multifunctionalized tetrahydro-1,2-oxazines (THOs) has been achieved by the organocatalyzed asymmetric tandem alpha-aminoxylation/aza-Michael reaction for the C-O/C-N bond formations in moderate to good yields with excellent diastereo- (>99:1 dr) and enantioselectivities (92% to >99% ee).

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