Stereoselective Synthesis of β‐Substituted β‐Amino Sulfones and Sulfonamides via Addition of Sulfonyl Anions to Chiral N‐Sulfinyl Imines.

A highly stereoselective synthesis of β-amino sulfones and sulfonamides via addition of sulfonyl anions to chiral N-sulfinyl imines is described. The addition reaction proceeds in good yield (75−99%) and stereoselectivity.

[1]  Jinbo Hu,et al.  Facile Synthesis of Chiral α‐Difluoromethyl Amines from N‐(tert‐Butylsulfinyl)aldimines , 2005 .

[2]  J. Alemán,et al.  Highly stereoselective benzylation of N-sulfinylketimines. , 2005, Journal of the American Chemical Society.

[3]  H. Mitsuya,et al.  Reduction of peptide character of HIV protease inhibitors that exhibit nanomolar potency against multidrug resistant HIV-1 strains. , 2003, Journal of medicinal chemistry.

[4]  Wei Zhu,et al.  A short synthesis of the HIV-protease inhibitor nelfinavir via a diastereoselective addition of ammonia to the α,β-unsaturated sulfoxide derived from (R)-glyceraldehyde acetonide , 2002 .

[5]  J. Ellman,et al.  N-tert-butanesulfinyl imines: versatile intermediates for the asymmetric synthesis of amines. , 2002, Accounts of chemical research.

[6]  Yan Guo,et al.  Phenoxyphenyl sulfone N-formylhydroxylamines (retrohydroxamates) as potent, selective, orally bioavailable matrix metalloproteinase inhibitors. , 2002, Journal of medicinal chemistry.

[7]  G. Decrescenzo,et al.  α-Amino-β-sulphone hydroxamates as potent MMP-13 inhibitors that spare MMP-1 , 2001 .

[8]  M. Naimi-Jamal,et al.  The LiClO4-Mediated Synthesis of β-(Dialkylamino) Sulfoxides and β-(Dialkylamino) Sulfones by Addition of α-Lithiated Salts of Sulfoxides and Sulfones to Aldehydes and (Trimethylsilyl)dialkylamines , 2000 .

[9]  I. Fernández,et al.  Additions of Enantiopure α-Sulfinyl Carbanions to (S)-N-Sulfinimines: Asymmetric Synthesis of β-Amino Sulfoxides and β-Αmino Alcohols , 2000 .

[10]  D. Enders,et al.  Asymmetric Synthesis of α‐Substituted β‐Amino Sulfones by Aza‐Michael Addition to Alkenyl Sulfones and Subsequent α‐Alkylation , 2000 .

[11]  J. Ellman,et al.  Synthesis of Enantiomerically Pure N-tert-Butanesulfinyl Imines (tert-Butanesulfinimines) by the Direct Condensation of tert-Butanesulfinamide with Aldehydes and Ketones , 1999 .

[12]  D. Enders,et al.  Enantioselective Synthesis ofβ-Amino Sulfones by aza-Michael Addition to Alkenyl Sulfones , 1999 .

[13]  T. Balasubramanian,et al.  Asymmetric synthesis of functionalized piperidine derivatives: synthesis of (S)-anatabine , 1998 .

[14]  T. Hoye,et al.  MTPA (Mosher) amides of cyclic secondary amines: Conformational aspects and a useful method for assignment of amine configuration , 1996 .

[15]  T. Kusumi,et al.  High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids , 1991 .

[16]  A. Spaltenstein,et al.  Synthesis of highly functionalized trans-alkene isosteres of dipeptides , 1989 .

[17]  M. Mladenova.  Addition of Lithium Reagents of N-Substituted Sulfonamides to Schiff Bases , 1986 .

[18]  A. McPhail,et al.  Stereoselective synthesis of beta-substituted beta-amino sulfones and sulfonamides via addition of sulfonyl anions to chiral N-sulfinyl imines. , 2006, Organic letters.

[19]  J. Castaǹer,et al.  Canfosfamide hydrochloride: Oncolytic DNA alkylating drug , 2004 .