55049-25-7Relevant academic research and scientific papers
Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether
Hari Babu, Madala,Ranjith Kumar, Gadi,Kant, Ruchir,Sridhar Reddy, Maddi
supporting information, p. 3894 - 3897 (2017/04/04)
Addition of arylboronic acids to directing group tethered acetylenes in a regio and stereoselective manner using an inexpensive catalytic system is achieved for the first time to access highly sought after allyl/homoallyl alcohol/amine units. The apparent vinylnickel intermediate was successfully trapped by the Michael electrophiles to get defined tri- and tetra-substituted olefins. An interesting selectivity switch was observed with internal alkynes.
Zinc-mediated α-regioselective Barbier-type cinnamylation reactions of aldehydes, ketones and esters
Zhao, Li-Ming,Gao, Hua-Shuai,Li, De-Feng,Dong, Jing,Sang, Lan-Lin,Ji, Jie
, p. 4359 - 4366 (2017/07/10)
We report a simple, efficient, and general method for the zinc-mediated regioselective cinnamylation of aldehydes and ketones under Barbier-type conditions in a one-pot synthesis affording the corresponding α-cinnamylated alcohols in moderate to excellent yields. Compared to the literature procedures, this approach is operationally simple, uses simple reactants, and provides direct access to linear α-cinnamylated alcohols with excellent regioselectivity. Experimental results suggest that the reactions proceed through the radical pathway. In addition, the reaction was found to be scalable to the gram-scale and the one-pot protocol is also applicable to less reactive esters leading to bishomoallylic alcohols which were valuable intermediates for desymmetrizing intramolecular Heck cyclization, allowing for the elaboration to functionalized building blocks.
Enantioselective synthesis of α-tri- and α-tetrasubstituted allylsilanes by copper-catalyzed asymmetric allylic substitution of allyl phosphates with silylboronates
Takeda, Momotaro,Shintani, Ryo,Hayashi, Tamio
, p. 5007 - 5017 (2013/07/11)
A copper/N-heterocyclic carbene-catalyzed asymmetric allylic substitution of allyl phosphates with a silylboronate has been developed to give highly enantioenriched allylsilanes. High regioselectivity has been achieved by employing NaOH as the base, and this catalyst system is effective for both γ-mono- and disubstituted allyl phosphates.
A stereoselective route to trans-2,5-disubstituted tetrahydrofurans
Kang,Hwang,Kim,Lim
, p. 5917 - 5920 (2007/10/02)
An efficient stereocontrolled route to trans-2,5-disubstituted tetrahydrofurans from trans-4-phenyl-3-buten-1-ol derivatives has been developed by using phenylselenyl chloride with zinc bromide in DME at -55°C.
Enantioselective Allylation of Aldehydes with an Optically Active Allylsilane
Hayashi, Tamio,Konishi, Mitsuo,Kumada, Makoto
, p. 281 - 282 (2007/10/02)
Reaction of aldehydes with an optically active allylsilane, (R)-3-phenyl-3-(trimethylsilyl)propene, in the presence of titanium chloride has been found to proceed with high enantioselectivity to produce optically active homoallylic alcohols of up to 91per
