84363-93-9

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 67883-63-0 (E)-3,7-dimethyl-1-tributylstannylocta-2,6-diene 
• 20536-36-1 neryl chloride 
• 372023-59-1 ((Z)-3,7-dimethyl-2,6-octadienyl)(trichloro)silane 

Relevant academic research and scientific papers

Facile Synthesis of Both syn and anti Homoallylic Alcohols from Allyl Chlorides via Organosilicon Intermediates

Highly regio- and diastereoselective synthesis of homoallylic alcohols from allyl chlorides via organosilicon intermediates are attained.While syn homoallylic alcohols were prepared from (Z)-allyl chlorides, anti homoallylic alcohols were obtained from (E)-allyl chlorides. 1-Chloro-2,4-pentadiene reacted at the γ position of the diene system regioselectively.

Facile and Highly Stereoselective Synthesis of Homoallylic Alcohols Using Organosilicon Intermediates

Allyltrichlorosilanes regioselectively reacted with aldehydes in N,N-dimethylformamide (DMF) without a catalyst to afford the corresponding homoallylic alcohols in high yields.The reactions proceeded under neutral conditions, and syn- and anti-homoallylic alcohols were stereoselectively obtained from (Z)- and (E)-allyltrichlorosilanes, respectively.In these reactions, DMF coordinated to the silicon atom of the allyltrichlorosilanes to form hypervalent silicates, which in turn reacted with aldehydes smoothly.Solvent effects in these reactions were also examined.The reactions were applied to the one-pot synthesis of homoallylic alcohols from allylic chlorides via organosilicon intermediates.While syn-homoallylic alcohols were prepared from (Z)-allyl chlorides, anti-homoallylic alcohols were obtained from (E)-allyl chlorides.Unique regioselectivities in the reactions of 1-chloro-2,4-pentadiene were also found.Finally, the one-pot synthesis of homoallylic alcohols from 1,3-dienes is reported.

STEREOSELECTIVE ACYCLIC SYNTHESIS VIA ALLYLMETALS: STRUCTURAL DEPENDENCE IN A LEWIS-ACID CATALYZED ADDITION OF ALLYLTINS TO ALDEHYDES

Lewis-acid catalyzed reaction of allyltins with aldehydes at -78 deg C provide homoallyl alcohols with high stereoselectivity; 2-alkenyltins in general provide erythro adducts preferentially with an erithro/threo ratio greater than 12/1, whereas only thre