1309861-32-2Relevant academic research and scientific papers
Palladium/H+-cocatalyzed kinetic resolution of tertiary propargylic alcohols
Zhang, Wanli,Ma, Shengming
, p. 6064 - 6067 (2018)
A new approach to not-readily-available optically active tertiary propargylic alcohols through palladium/H+-cocatalyzed carboxylation of racemic tertiary propargylic alcohols with CO and MeOH has been described. Both enantiomers can be obtained with no less than 90% ee utilizing (R) or (S)-DTBM-Segphos. Various transformations of the optically active alcohols have been demonstrated.
Method for directly constructing tetra-substituted allenic acid compound with high optical activity
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Paragraph 0045-0048; 0189-0191, (2020/07/15)
The invention discloses a method for directly constructing a tetra-substituted allenic acid compound with high optical activity, wherein tertiary propargyl alcohol, carbon monoxide and water react inan organic solvent under the actions of a palladium catalyst, a chiral diphosphine ligand, a monophosphine ligand and organic phosphoric acid to directly construct an axially chiral allenic acid compound with high optical activity in one step. The method has characteristics of simple operation, easily available raw materials and reagents, mild reaction conditions, wide substrate universality, goodfunctional group compatibility and high reaction enantioselectivity (90%-99% ee). According to the invention, the allenic acid compound with high optical activity can be used as an important intermediate for constructing compounds such as gamma-butyrolactone compounds containing tetra-substituted chiral quaternary carbon centers, tetra-substituted allenol and the like.
Kinetic Resolution of Tertiary Propargylic Alcohols by Enantioselective Cu?H-Catalyzed Si?O Coupling
Seliger, Jan,Dong, Xichang,Oestreich, Martin
supporting information, p. 1970 - 1974 (2019/01/29)
A broad range of tertiary propargylic alcohols were kinetically resolved by catalyst-controlled enantioselective silylation. This non-enzymatic kinetic resolution is catalyzed by a Cu?H species and makes use of the commercially available precatalyst MesCu/(R,R)-Ph-BPE and a simple hydrosilane as the resolving reagent. Both alkyl,aryl- as well as dialkyl-substituted propargylic alcohols participate, and especially high selectivity factors are achieved when the alkyne terminus carries a TIPS group, which also enables facile post-functionalization in this position (s up to 207).
Lithium binaphtholate-catalyzed asymmetric addition of lithium acetylides to carbonyl compounds
Kotani, Shunsuke,Kukita, Kenji,Tanaka, Kana,Ichibakase, Tomonori,Nakajima, Makoto
, p. 4817 - 4825 (2014/06/23)
The asymmetric addition of lithium acetylides to carbonyl compounds in the presence of a chiral lithium binaphtholate catalyst was developed. A procedure involving the slow addition of carbonyl compounds to lithium acetylides improved the enantioselectivi
Lithium acetylides as alkynylating reagents for the enantioselective alkynylation of ketones catalyzed by lithium binaphtholate
Tanaka, Kana,Kukita, Kenji,Ichibakase, Tomonori,Kotani, Shunsuke,Nakajima, Makoto
supporting information; experimental part, p. 5614 - 5616 (2011/06/21)
Chiral lithium binaphtholate effectively catalyzed the enantioselective alkynylation of ketones using lithium acetylide as an alkynylating agent. This is the first example of the catalytic enantioselective addition of lithium acetylide to carbonyl compoun
