+ Site Statistics
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Stereoselective synthesis of beta-substituted beta-amino sulfones and sulfonamides via addition of sulfonyl anions to chiral N-sulfinyl imines



Stereoselective synthesis of beta-substituted beta-amino sulfones and sulfonamides via addition of sulfonyl anions to chiral N-sulfinyl imines



Organic Letters 8(4): 789-792



[reaction: see text] A highly stereoselective synthesis of beta-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.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 050384805

Download citation: RISBibTeXText

PMID: 16468768

DOI: 10.1021/ol053132b


Related references

Stereoselective nucleophilic addition of chiral lithium enolates to (N-tosyl)imines: Enantioselective synthesis of beta-aryl-beta-amino acid derivatives. Tetrahedron Letters 43(17): 3209-3212, 2002

Stereoselective Michael Addition of Glycine Anions to Chiral Fischer Alkenylcarbene Complexes. Asymmetric Synthesis of beta-Substituted Glutamic Acids. Journal of Organic Chemistry 64(18): 6554-6565, 1999

Asymmetric synthesis of alpha-substituted beta-amino ketones from sulfinimines (N-sulfinyl imines). synthesis of the indolizidine alkaloid (-)-223A. Journal of the American Chemical Society 127(23): 8398-8407, 2005

Vinylaluminum addition to sulfinimines (N-sulfinyl imines). Asymmetric synthesis of anti-alpha-alkyl beta-amino esters. Journal of Organic Chemistry 74(7): 2798-2803, 2009

Addition of a Reformatsky reagent to N-anthracene-9-sulfonyl and related imines Synthesis of protected beta-amino acids. Tetrahedron 49(48): 11329-11340, 1993

Stereoselective addition reactions of chiral alpha sulfinyl ketimine anions with ene esters asymmetric total synthesis of elaeokanines a and b. Abstracts of Papers American Chemical Society 198: ORGN 9, 1989

Diastereoselective addition of chlorotitanium enolate of N-acyl thiazolidinethione to O-methyl oximes: a novel, stereoselective synthesis of alpha,beta-disubstituted beta-amino carbonyl compounds via chiral auxiliary mediated azetine formation. Journal of the American Chemical Society 125(13): 3690-3691, 2003

Stereoselective synthesis of racemic alpha-amino-acid derivatives with a beta-lactam skeleton: Application of the Staudinger reaction to chiral imines of methylglyoxylate. Tetrahedron 54(38): 11501-11516, 1998

Enantioselective synthesis of chiral sulfones by Rh-catalyzed asymmetric addition of boronic acids to alpha,beta-unsaturated 2-pyridyl sulfones. Journal of Organic Chemistry 72(26): 9924-9935, 2007

An effective preparation of sulfonyl- or sulfinyl-substituted fluorinated alkenes and their stereoselective addition-elimination reactions with organocuprates. Chemistry An Asian Journal 5(8): 1846-1853, 2010

Highly stereoselective synthesis of beta-lactams by condensation of the titanium enolate of a chiral 2-pyridylthioester with chiral imines. Tetrahedron 51(36): 10025-10032, 1995

Enantioselective Synthesis of -Amino--sulfonyl Phosphonates with a Tetrasubstituted Chiral -Carbon via Quinine-Squaramide-Catalyzed Michael Addition of Nitrophosphonates to Vinyl Sulfones. Advanced Synthesis & Catalysis 355(7): 1265-1270, 2013

Asymmetric synthesis with chiral beta lactams highly stereoselective alkylation and aldol reaction of a chiral 3 amino 4 styryl beta lactam. Tetrahedron Letters 31(7): 977-980, 1990

Chlorotitanium enolate addition to aldimines: a stereoselective route to alpha-oxy-beta-substituted-beta-amino esters. Journal of Organic Chemistry 65(19): 6264-6267, 2000

1,6-Asymmetric induction during the conjugate addition of arylcopper reagents to a chiral sulfinyl-substituted pyrrolyl alpha,beta-unsaturated amide. Chemical and Pharmaceutical Bulletin 49(12): 1609-1614, 2001