Asymmetric Synthesis of Novel Vicinal Amino Alcohols via Intramolecular Ketone-N-sulfinylimine Pinacol-Type Reductive Coupling Promoted by SmI₂

Abstract

A novel intramolecular asymmetric ketone-N-sulfinylimine pinacol-type reductive coupling reaction induced by SmI₂ was reported. A series of 1-amino-1,2,3,4-tetrahydronaphthalen-2-carbinols were obtained in moderate to good yields with excellent ee and high dr.

[Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.]

GRAPHICAL ABSTRACT

Keywords:

• Asymmetric synthesis
• N-sulfinylimine
• samarium diiodide
• vicinal amino alcohol

Notes

^a All reactions were reacted for 3 h.

^b Isolated yield of the single diastereoisomer.

^a dr was determined by ¹H NMR of the crude products.

^b Isolated yields of all diastereomers.