898237-80-4

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 172748-23-1 (-)-(Z)-(1R,2R)-2-isopropyl-4-[(S)-N-methyl-S-phenylsulfonimidoyl]-1-phenylbut-3-en-1-ol 

Downstream Products

• 1058213-68-5 C₂₆H₃₉NO₂SSi 
• 1058214-00-8 tert-butyl [(1R,2R)-2-isopropyl-4-methyl-1-phenylpent-3-enyloxy]dimethylsilane 
• 1058213-98-1 C₂₀H₃₃⁽²⁾HOSi 
• 1058214-02-0 tert-butyl ((1R,2R,E)-2-isopropyl-1-phenylpent-3-enyloxy)dimethylsilane 
• 1058214-04-2 (R,Z)-ethyl 6-((R)-(tert-butyldimethylsilyloxy)(phenyl)methyl)-4,7-dimethyloct-4-enoate 

Relevant academic research and scientific papers

Anionic cross-coupling reaction of α-metallated alkenyl sulfoximines and alkenyl sulfoximines with cuprates featuring a 1,2-metal-ate rearrangement of sulfoximine-substituted higher order alkenyl cuprates and an α-metallation of alkenyl sulfoximines by cuprates

(E)- and (Z)-configured αlithioalkenyl sulfoximines, which are available through lithiation of the corresponding alkenyl sulfoximines, undergo a anionic cross-coupling reaction (ACCR) with organocuprates with formation of the corresponding alkenyl cuprates and sulfinamide. The alkenyl cuprates can be trapped by electrophiles. The ACCR presumably proceeds via the formation of a higher-order sulfoximine-substituted alkenyl cuprate, which undergoes a 1,2-metalate rearrangement whereby the sulfoximine group acts as the nucleofuge. The parent (E)- and (Z)-configured alkenyl sulfoximines suffer upon treatment with an organocuprate a deprotonation at the α-position with formation of the corresponding α-cuprioalkenyl sulfoximines. These derivatives also enter into a similar ACCR with organocuprates. The ACCR of sulfoximines substituted homoallylic alcohols allows a stereoselective access to enantio- and diastereopure substituted homoallylic alcohols.