143701-23-9Relevant academic research and scientific papers
Aldehyde allylation with allylboronates providing α-addition products
Kobayashi, Shu,Endo, Toshimitsu,Schneider, Uwe,Ueno, Masaharu
supporting information; experimental part, p. 1260 - 1262 (2010/07/05)
Zn(OH)2-catalyzed allylation reactions of allylboronates with aldehydes proceeded smoothly in aqueous media; when α-substituted allylboronates were employed, the α-addition products were obtained exclusively, and syn-adducts were formed selecti
Copper-catalyzed reactions of organotitanium reagents. Highly selective SN2′-allylation and conjugate addition
Arai, Masayuki,Lipshutz, Bruce H.,Nakamura, Eiichi
, p. 5709 - 5718 (2007/10/02)
In the presence of a catalytic amount of CuI·ILiCl, alkyltitanium (RTi(O-I-Pr)3) and titanate reagents (RnTi(O-i-Pr)5-nLi) undergo highly selective SN2′-alkylation reactions with allylic chlorides and allylic diethylphosphates in high yields. The regioselectivity of the reaction is as high as 99.8%. The reaction proceeds with excellent anti-stereoselectivity with respect to the nucleophile and the leaving group, and exhibits high 1,2-anti-diastereoselectivity with a δ-chiral allylic chloride. The catalytic copper reagent is also a mild agent to transfer an alkyl group to an enone in the presence of Me3SiCl. The alkyltitanium-based catalytic reagent selectively reacts with an allylic phosphate rather than with an enone, while in the presence of a silicon activator, it reacts preferentially with the enone rather than with the phosphate. 1H NMR studies on a mixture of Me2CuLi and TiCl(O-i-Pr)3 provided information on reagent composition.
