Stereoselective synthesis of allylic sulfoximines from S-(chloromethyl)-N-methyl-S-phenylsulfoximine and alkenyl cuprates

Synlett

Volumn , Issue 1, 1998, Pages 99-101

  Boßhammer, Stephan ^a   Gais, Hans Joachim ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 4244113382     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-985344     Document Type: Article

References (23)

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15. 12NOS: 194.06396. Found: 194.06378. (+)-(S,Z)-N-Methyl-S-phenyl-S-(3-phenyl-2-propenyl)-sulfoximine (4c). To a solution of (Z)-β-bromostyrene (555 mg, 3.03 mmol) in THF-ether-n-pentane, 4:1:1 (15 mL) was added dropwise at -120°C a solution of t-BuLi (6.06 mmol, 1.39 mL of 1.6 M in n-pentane). After stirring the mixture for 45 min, it was added to a suspension of CuCN (136 mg, 1.52 mmol) in THF (5 mL). The mixture was stirred for 45 min at -35°C to form a brownish solution of 3c. The mixture was cooled to -78°C and a solution of 2a (309 mg, 1.52 mmol) in THF (5 mL) added dropwise.
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