Trialkylborane-Mediated Multicomponent Reaction for the Diastereoselective Synthesis of Anti-δ,δ-Disubstituted Homoallylic Alcohols
The trialkylborane/O2-mediated reaction of propargyl acetates having a tributylstannyl group at an alkyne terminus with aldehydes in a THF-H2O solvent system gave anti-δ,δ-disubstituted homoallylic alcohols with good to high diastereoselectivity. Intriguingly, two alkyl groups derived from trialkylborane were embedded into the reaction product. The trialkylborane plays a key role not only as a radical initiator but also as a source of alkyl radicals.
Horino, Yoshikazu,Murakami, Miki,Aimono, Ataru,Lee, Jun Hee,Abe, Hitoshi
supporting information
p. 476 - 480
(2019/01/14)
Palladium-Catalyzed Three-Component Reaction of 3-(Tri-n- butylstannyl)allyl Acetates, Aldehydes, and Triorganoboranes: An Alternative to the Carbonyl Allylation Using α,γ-Substituted Allylic Tin Reagents
A three-component reaction of 3-(tri-n-butylstannyl)allyl acetates, aldehydes, and triorganoboranes in the presence of a palladium-Xantphos catalyst system predominately gave (E)-anti-homoallylic alcohols with high diastereoselectivity and good to high levels of alkene stereocontrol. An efficient chirality transfer was observed when an enantioenriched substrate was employed. The reaction was initiated by the formation of an allylic gem-palladium/stannyl intermediate, which subsequently underwent allylation of the aldehyde by an allyltributyltin followed by a coupling reaction of the in-situ-generated (E)-vinylpalladium acetate with the triorganoborane.
Horino, Yoshikazu,Sugata, Miki,Abe, Hitoshi
supporting information
p. 1023 - 1028
(2016/04/19)
Proline-Catalyzed Cyclization Reaction for the Synthesis of Naphthostyrils: Application to the Total Synthesis of Prioline
A new method for the synthesis of naphthostyrils is described. In this method, a sequential Stille coupling and proline-catalyzed cyclization procedure is employed for the reaction of 4-bromooxindoles and β-tributylstannyl-α,β-unsaturated ketones. The uti
Park, Kyeong-Yong,Song, Ha-Jeong,Heo, Jung-Nyoung
p. 3197 - 3205
(2015/11/03)
Non-Pd transition metal-catalyzed hydrostannations: Bu3SnF/PMHS as a tin hydride source
Molybdenum, cobalt, nickel, ruthenium, and rhodium catalyzed alkyne hydrostannations using in situ generated Bu3SnH were studied. In most cases, Bu3SnF+polymethylhydrosiloxane (PMHS) performed well as the in situ source of Bu3/
Maleczka Jr., Robert E.,Ghosh, Banibrata,Gallagher, William P.,Baker, Aaron J.,Muchnij, Jill A.,Szymanski, Amy L.
p. 4000 - 4008
(2013/06/27)
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