Asymmetric synthesis of chiral sulfoxides and sulfinimines by using N-sulfinylsultam

Tetrahedron Letters

Volumn 38, Issue 16, 1997, Pages 2825-2828

  Oppolzer, Wolfgang ^a   Froelich, Olivier ^a,b   Wiaux Zamar, Chantal ^a,c   Bernardinelli, Gérald ^a  

^a UNIVERSITY OF GENEVA   (Switzerland)

^b NOVARTIS PHARMA AG   (Switzerland)

^c Email:   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

SULFINAMIDE; SULFOXIDE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY; THERMODYNAMICS;

EID: 0031006429     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00472-3     Document Type: Article

References (35)

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24. All attempts to prepare 2 by oxidation of the N-(p-tolylthio)bornane-10,2-sultam showed poor diastereoselectivity.
25. The reagent 2-(R) has exhibited a shelf life of at least 2 years at -2O°C with no sign of decomposition.
26. 2: C: 57.68% H: 6.51% N: 4.08%, calc: C: 57.76% H: 6.56% N: 3.96%.
27. 2(F)) for 1998 observed reflections [|Fo| ≥ 4σ(Fo)]
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35. General procedure for the preparation of sulfinimines starting from enolisable aldehydes (Method A) To a solution of 2-(R) (50 mg, 0.142 mmol) in THF (1.5 mL) at -78°C was slowly added a 1 M hexane solution of LiHMDS (156ml, 0.156 mmol). The clear solution was stirred at -78°C for 1 h and 1 equiv. of water was added (solution of 100 μl water in 1 ml of THF). The temperature was raised to-20°C, the mixture was stirred for 10 min and 1.1 equiv. of the freshly distilled aldehyde was added. The reaction was stirred for 2-3 h and the temperature slowly raised to 5°C. The mixture was filtered on celite, concentrated in vacuo and the resultant oil was purified by FC on silica gel.