137943-35-2

Upstream product

• 79026-61-2 (R)-3-benzyloxy-2-methylpropanal 
• 137920-09-3 3-(tributylstannyl)-3,4-hexadiene 

Downstream Products

• 137943-36-3 (2R,4S)-(Z)-1-(benzyloxy)-2,4-dimethyl-5-octen-3-one 
• 102210-04-8 (2R,3S,4R)-5-Benzyloxy-2,4-dimethyl-pentane-1,3-diol 
• 138124-14-8 (2R,3R,4R)-2,4-dimethyl-5-(benzyloxy)-1,3-(isopropylidenedioxy)pentane 
• 98039-09-9 (2S,3R,4R)-5-Benzyloxy-3-hydroxy-2,4-dimethyl-pentanal 

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.