133910-87-9

Upstream product

• 81445-44-5 (S)-2-(benzyloxy)propanal 
• 171011-57-7 Acetic acid 2-tributylstannanyl-penta-2,3-dienyl ester 

Downstream Products

• 137920-25-3 Acetic acid (Z)-(4R,6S)-6-benzyloxy-5-hydroxy-4-methyl-hept-2-enyl ester 
• 137920-24-2 (2R,4R)-(Z)-2-benzyloxy-4-methyl-7-acetoxy-5-penten-3-one 
• 1027324-32-8 (2S,3S,4S)-4-Benzyloxy-3-hydroxy-2-methyl-pentanal 
• 137943-34-1 (2R,3S,4S)-2-methyl-4-(benzyloxy)-1,3-(isopropylidenedioxy)pentane 
• 1026597-32-9 (2R,3S,4S)-4-Benzyloxy-2-methyl-pentane-1,3-diol 
• 137920-25-3 Acetic acid (Z)-(4R,5S,6S)-6-benzyloxy-5-hydroxy-4-methyl-hept-2-enyl ester 

Relevant academic research and scientific papers

Synthesis of Enantioenriched Homopropargylic Alcohols through Diastereoselective SE' Additions of Chiral Allenylstannanes to Aldehydes

Allenylstannanes (S)-4 and (R)-4, available in ca. 90percent ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by SN2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi*CuBr*Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity.With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4.BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51.Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.

Highly Diastereoselective SE' Additions of Enantioenriched Allenylstannanes to (S)-2-(Benzyloxy)propanol

The BF3-promoted addition of (S)-allenylstannane (S)-6 to aldehyde 16 afforded a 68:32 mixture of diastereomeric homopropargylic alcohols 17 and 18 whereas MgBr2-promoted addition gave adduct 17 as the exclusive product.The (R)-allenylstannane (R)-6, on t