Tetrahedron: Asymmetry

SmI 2-coupling reaction of chiral non-racemic α-bromo-α′-sulfinyl ketones with imines: synthesis of enantiomerically pure 2-methyl-3-amino-1-ol moieties

M Barbarotto, J Geist, S Choppin, F Colobert

Index: Barbarotto, Marie; Geist, Julie; Choppin, Sabine; Colobert, Francoise Tetrahedron Asymmetry, 2009 , vol. 20, # 24 p. 2780 - 2787

Full Text: HTML

Citation Number: 11

Abstract

Chiral non-racemic α-bromo-α′-sulfinyl ketones were shown to react with imines in the presence of SmI2 to give the corresponding 1, 3-aminoketo derivatives with good syn- diastereoselectivity. Further reduction of these adducts either with DIBAL-H only or with DIBAL-H in the presence of Yb (OTf) 3 afforded syn-and anti-2-methyl-3-amino-1-ol moieties, respectively, in good yields and diastereoselectivities.

Related Articles:

Triarylmethyl chlorides as novel, efficient, and mild organic catalysts for the synthesis of N-sulfonyl imines under neutral conditions

[Patel, Rajesh; Srivastava, Vishnu P.; Yadav, La Dhar S. Advanced Synthesis and Catalysis, 2010 , vol. 352, # 10 p. 1610 - 1614]

Hammett investigation of iodide-ion-induced deoxygenative reduction of 2-aryl'sulphonyl-3-aryloxaziridines in methanol-water (50% v/v).

[Knipe, A. C.; McAuley, I. E.; Khandelwal, Y.; Kansal, V. K. Tetrahedron Letters, 1984 , vol. 25, # 13 p. 1411 - 1414]

More Articles...