210552-40-2

Basic information

• Product Name: (+)-(S)-1-Phenyl-3,4,5,6-tetrahydro[1,2]thiazin-1-oxide
• Synonyms: (+)-(S)-1-Phenyl-3,4,5,6-tetrahydro[1,2]thiazin-1-oxide
• CAS NO: 210552-40-2
• Molecular Weight: 195.285
• Mol File: 210552-40-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (+)-(S)-1-Phenyl-3,4,5,6-tetrahydro[1,2]thiazin-1-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(S)-1-Phenyl-3,4,5,6-tetrahydro[1,2]thiazin-1-oxide(210552-40-2)
• EPA Substance Registry System: (+)-(S)-1-Phenyl-3,4,5,6-tetrahydro[1,2]thiazin-1-oxide(210552-40-2)

Safety Data

• Hazardous Substances Data: 210552-40-2(Hazardous Substances Data)

Upstream product

• 210552-36-6 (+)-(S)-N-(3-Hydroxypropyl)-S-methyl-S-phenylsulfoximine 
• 4381-25-3 (S)-S-methyl-S-phenylsulfoximine 
• 210552-38-8 (+)-(S)-S-Methyl-S-phenyl-N-(3-p-tosyloxypropyl)sulfoximine 

Downstream Products

• 1305338-61-7 (+)-(1S,6S)-6-(trimethylsilyl)methyl-1-phenyl-3,4,5,6-tetrahydro-1λ4-1,2-thiazine 1-oxide 
• 1305338-88-8 C₁₄H₂₁⁽²⁾H₂NOSSi 
• 1305338-87-7 C₁₄H₂₂⁽²⁾HNOSSi 
• 1305338-86-6 (1S,6R)-6-(trimethylsilyl)methyl-1-phenyl-3,4,5,6-tetrahydro-1λ4-1,2-thiazine 1-oxide 
• 1305338-85-5 C₁₄H₂₂⁽²⁾HNOSSi 

Relevant articles and documents

Synthesis and alkylation of cyclic α-sulfonimidoyl carbanions: Non- transferable chiral carbanionic ligands in copper-mediated enantioselective conjugate addition

The cyclic sulfoximines 4a and 4b have been prepared from (+)-(S)-S- methyl-S-phenylsulfoximine (1). Deprotonation of 4a and 4b and alkylation of lithiosulfoximines Li-4a and Li-4b gave α-alkyl substituted sulfoximines 5a (89% de), 5b (90% de), 6a (≤98% de), 6b (≤98% de), 7b (≤98% de) and 8b (≤98% de). The configuration of 6b was determined by X-ray structure analysis. Consecutive treatment of 5b, 6b and 8b with BuLi and CF3CO2H gave epimers epi-5b (64% de), epi-6b (89% de) and epi-8b (81% de). α,α -Dialkyl substituted sulfoximines 9 (≤98% de) and epi-9 (≤98% de) were obtained by alkylation of Li-5b and Li-6b. Conjugate addition of cuprates 11-14, containing the acyclic sulfonimidoyl carbanions Ia-c, to cyclohex-2-en-1-one gave ketones 15 and 16 in good yields but with low asymmetric induction (8- 49% ee). However, conjugate addition of cuprates 19b, 20b, 21b and 22b, derived from the cyclic lithiosulfoximines Li-7b and Li-8b, to cyclopent-2- en-1-one, cyclohex-2-en-1-one and cyclohept-2-en-1-one gave ketones 15a-c, 23b and 24b with good to high asymmetric inductions (77-99% ee) in good yields. The bicyclic ketone 27 (79% ee) was prepared from cyclohex-2-en-1- one via 24b in three steps.