77396-98-6

Upstream product

• 433294-76-9 (E)-5-((tert-butyldimethylsilyl)oxy)-pent-3-en-2-ol 
• 81445-44-5 (S)-2-(benzyloxy)propanal 
• 137329-31-8 (E)-(S)-4-Benzyloxy-pent-2-enoic acid methyl ester 

Downstream Products

• 119204-56-7 Dithiocarbonic acid S-[1-((S)-1-benzyloxy-ethyl)-allyl] ester S-methyl ester 
• 433294-77-0 (E)-4-benzyloxy-2-penten-1-yl acetate 
• 145914-28-9 (R)-2-((S)-1-Benzyloxy-ethyl)-but-3-ene-1-thiol 
• 145914-28-9 (S)-2-((S)-1-Benzyloxy-ethyl)-but-3-ene-1-thiol 
• 145914-30-3 C₁₉H₂₂OS₂ 
• 112980-57-1 Thioacetic acid S-((Z)-4-benzyloxy-pent-2-enyl) ester 

Relevant academic research and scientific papers

Diastereoselective reactions of δ-oxy-substituted allylic acetates with organocopper reagents

SN2′ (γ) substitutions of δ-substituted allylic acetates with Grignard reagents and copper catalysts proceed with high diastereoselectivities. With benzyloxy, methoxymethoxy, and tert-butyldimethylsiloxy groups, reactions favor the anti-isomer with selectivities up to anti:syn = >99:1. With a hydroxyl group, selectivities are reversed and the syn-isomer is favored with selectivities up to anti:syn = 1:99.

AN OBSERVATION OF DIASTEREOFACE SELECTIVITY IN THERMAL REACTIONS BETWEEN δ-ALKOXYALLYLSTANNANES AND ALDEHYDES

The δ-alkoxyallylstannanes (4) and (5) react stereoselectively on heating with p-nitrobenzaldehyde to provide the homoallylic alcohols (14) - (17), with (14) : (15) = 82 : 18; (16) : (17) = 73 : 27