138124-47-7

Upstream product

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

Downstream Products

• 98039-09-9 (2R,3S,4R)-5-Benzyloxy-3-hydroxy-2,4-dimethyl-pentanal 
• 98167-13-6 (2R,3R,4S)-1-benzyloxy-3,5-dihydroxy-2,4-dimethylpentane 
• 98102-72-8 (2S,3S,4R)-2,4-dimethyl-5-(benzyloxy)-1,3-(isopropylidenedioxy)pentane 
• 137943-36-3 (2R,4S)-(Z)-1-(benzyloxy)-2,4-dimethyl-5-octen-3-one 

Relevant academic research and scientific papers

Synthesis of syn,syn; anti,syn; syn,anti; and anti,anti Stereotriads from a Single Pair of Enantiomeric Reagents

The stannanes (S)-1a, (R)-1b, and (S)-1c add to (S)- and (R)-2-methyl-3-(benzyloxy)propanal ((S)-2 and (R)-2) to afford the syn,syn (BF3*OEt2 promotion), syn,anti (MgBr2*OEt2 promotion), anti,anti (SnCl4-derived reagent in CH2Cl2), and anti,syn (SnCl4-derived reagent in hexane) stereotriad adducts 3, 4, 6, and 7.

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.