80317-46-0Relevant articles and documents
Highly Regio- And Enantioselective Reductive Coupling of Alkynes and Aldehydes via Photoredox Cobalt Dual Catalysis
Li, Yan-Lin,Zhang, Shi-Qi,Chen, Jie,Xia, Ji-Bao
supporting information, p. 7306 - 7313 (2021/05/26)
A Co-catalyzed highly regio- and enantioselective reductive coupling of alkynes and aldehydes has been developed under visible light photoredox dual catalysis. A variety of enantioenriched allylic alcohols have been obtained by using unsymmetrical internal alkynes and commercially available catalyst, chiral ligand, and reagents. It is noteworthy that this approach has considerable advantages, such as excellent regio- (>95:5 for >40 examples), stereo- (up to >95:5 E/Z), and enantioselectivity (92-99% ee, >35 examples) control, mild reaction conditions, broad substrate scope, and good functional group compatibility, making it a great improvement to enantioselective alkyne-aldehyde reductive coupling reactions.
Nickel-Catalyzed Reductive Coupling of Aldehydes with Alkynes Mediated by Alcohol?
Zheng, Yan-Long,Ye, Mengchun
supporting information, p. 489 - 493 (2020/04/23)
A nickel-catalyzed reductive coupling of aldehydes with alkynes using 1-phenylethanol as reducing agent has been developed. The key achievement of this work is that we demonstrate environmentally benign 1-phenylethanol can serve as a viable alternative reducing agent to Et3B, ZnEt2 and R3SiH for the nickel-catalyzed reductive coupling reaction of aldehyde and alkynes.
Rhodium promoted isomerisation of allylic alkoxides: A new method for enolate anion formation
Gazzard, Lewis J.,Motherwell, William B.,Sandham, David A.
, p. 979 - 993 (2007/10/03)
Transition metal mediated isomerisation of allylic alkoxides is presented as a new method for enolate anion generation. The scope and limitations of enolate formation with the catalysts [Rh(dppe)(THF)2]+ClO4- and (Ph3P)3RhCl are explored and the synthetic potential of the methodology demonstrated in the stereoselective formation and reactions of certain ketone and aldehyde enolates.
Episulfone substitution and ring-opening reactions via α-sulfonyl carbanion intermediates
Dishington, Allan P.,Douthwaite, Richard E.,Mortlock, Andrew,Muccioli, Adriano B.,Simpkins, Nigel S.
, p. 323 - 337 (2007/10/03)
Three-membered cyclic sulfones undergo substitution on treatment with base-electrophile mixtures, such as LDA-Me3SiCl and Bu′-P4 phosphazene base-PhCHO, to give either substituted episulfones or the corresponding alkenes following loss of SO2. The structure of a trisilylated episulfone product, 2a, was determined by X-ray crystallography. In the absence of Me3SiCl, reaction of episulfones with lithium diisopropylamide results in ring-opening to give alkenyl sulfinate intermediates, which can be alkylated to give (E)-alkenyl sulfone products in stereoselective fashion.
Synthesis of (E)-1-Aryl-2-methyl-3-alkyl-2-propen-1-ones via Allylic Sulfoxide-Sulfenate Ester Rearrangements
Goodwin, Thomas E.,Ratcliff, David G.,Crowder, C. Michael,Seitzinger, Newton K.
, p. 815 - 820 (2007/10/02)
A synthon for vinyl anion 2 has been designed as the cornerstone for a versatile synthesis of (E)-1-aryl-2-methyl-3-alkyl-2-propen-1-ones (1).The choice of the allylic sulfoxide-sulfenate ester rearrangement as a synthesis conduit leads to formation of the desired E isomers stereoselectively.Attempted tetrahydropyran ring opening of enone 7c was not successful.
