131483-72-2Relevant academic research and scientific papers
Lewis Acid Promoted Additions of γ-Alkoxy- and -(Silyloxy)crotylstannanes to (S)-2-(Benzyloxy)propanal
Marshall, James A.,Jablonowsky, Jill A.,Luke, George P.
, p. 7825 - 7832 (2007/10/02)
Additions of the γ-oxygenated allylic stannane MOM ethers (R)-1a, (S)-1a, and silyl ethers (R)-1b, (S)-1b to (S)-2-(benzyloxy)propanal (2) in the presence of BF3*OEt2 and MgBr2 were examined in order to establish matched and mismatched preferences.In the
Diastereoselective Additions of Enantioenriched (γ-Alkoxyallyl)stannanes to α-Alkoxy Aldehydes: A Synthetic Route to Carbohydrates
Marshall, James A.,Luke, George P.
, p. 483 - 485 (2007/10/02)
BF3*OEt2-promoted additions of the (S)-(γ-alkoxyallyl)stannane 3-(S) to the (R)-α-alkoxy aldehydes 13 and 18 affords the syn adducts 14 and 19 with greater than 90:10 diastereoselectivity.With MgBr2 as the catalyst addition to the (S)-α-alkoxy aldehyde 4 is most selective (97:3) with the (S)-(γ-alkoxyallyl)stannane 3-(S) whereas BF3-promoted addition to 4 is most selective (92:8) with the R enantiomer 3-(R).
