889869-54-9Relevant articles and documents
Regiospecific hydration of γ-hydroxy-α,β-acetylenic esters: A novel asymmetric synthesis of tetronic acids
Rajaram, Amaresh R.,Pu, Lin
, p. 2019 - 2021 (2006)
The optically active γ-hydroxy-α,β-acetylenic esters are obtained from the enantioselective reaction of methyl propiolate with both aliphatic and aromatic aldehydes. These compounds can undergo regiospecific hydration in the presence of Zeise's dimer, [Pt
Highly enantioselective synthesis of γ-hydroxy-α,β- acetylenic esters catalyzed by a β-sulfonamide alcohol
Lin, Li,Jiang, Xianxing,Liu, Weixia,Qiu, Li,Xu, Zhaoqing,Xu, Jiangke,Chan, Albert S. C.,Wang, Rui
, p. 2329 - 2332 (2007)
This work concerns the asymmetric addition of methyl propiolate to aldehydes with 1,2-dimethoxyethane (DME) as additive and β-sulfonamide alcohol titanium complex as a catalyst. The reactions proceeded under mild conditions and gave the highly functionali
Development of Zn-prophenol-catalyzed asymmetric alkyne addition: Synthesis of chiral propargylic alcohols
Trost, Barry M.,Bartlett, Mark J.,Weiss, Andrew H.,Vonwangelin, Axel Jacobi,Chan, Vincent S.
supporting information, p. 16498 - 16509 (2013/02/23)
The development of a general and practical zinc-catalyzed enantioselective alkyne addition methodology is reported. The commercially available ProPhenol ligand (1) has facilitated the addition of a wide range of zinc alkynylides to aryl, aliphatic, and α,β-unsaturated aldehydes in high yield and enantioselectivity. New insights into the mechanism of this reaction have resulted in a significant reduction in reagent stoichiometry, enabling the use of precious alkynes and avoiding the use of excess dimethylzinc. The enantioenriched propargylic alcohols from this reaction serve as versatile synthetic intermediates and have enabled efficient syntheses of several complex natural products. A precious few: A general and practical zinc-catalyzed enantioselective alkyne addition methodology is reported (see scheme). New insights into the mechanism of this reaction have resulted in a significant reduction in reagent stoichiometry, enabling the use of precious alkynes and avoiding the use of excess dimethylzinc. This methodology has enabled the efficient synthesis of several complex natural products.
Synthesis of a C1 symmetric BINOL-terpyridine ligand and highly enantioselective methyl propiolate addition to aromatic aldehydes
Chen, Xi,Chen, Wei,Wang, Li,Yu, Xiao-Qi,Huang, De-Shun,Pu, Lin
supporting information; experimental part, p. 1990 - 1993 (2010/04/24)
A novel C1 symmetric BINOL-terpyridine ligand (R)-5 is synthesized. This ligand in combination with ZnEt2 and Ti(OiPr)4 is found to catalyze the highly enantioselective reaction (up to 98% ee) of methyl propiola
Reactivity of γ-hydroxy-α-acetylenic esters with amines: Facile synthesis of the optically active 4-amino-2(5H)-furanones
Zhou, Li-Hong,Yu, Xiao-Qi,Pu, Lin
experimental part, p. 2013 - 2017 (2009/08/07)
A convenient synthesis of the optically active 4-amino-2(5H)-furanones is discovered by combining an asymmetric alkyne addition to aldehydes and a subsequent aliphatic amine addition. Both steps can be conducted at room temperature and the products are obtained with high enantioselectivity (84-90% ee). The 4-amino-2(5H)-furanones are also found to undergo very facile electrophilic substitution reactions.
Highly enantioselective addition of methyl propiolate to aldehydes catalyzed by a titanium(IV) complex of a β-hydroxy amide
Xu, Tao,Liang, Chao,Cai, Yan,Li, Jian,Li, Ya-Min,Hui, Xin-Ping
experimental part, p. 2733 - 2736 (2010/04/26)
Three chiral β-hydroxy amide ligands were prepared by the reaction of benzyl chloride with amino alcohols derived from l-tyrosine. The titanium(IV) complex of chiral ligand 4a was found to be an effective catalyst for the asymmetric addition of methyl propiolate to aliphatic and aromatic aldehydes. The γ-hydroxy-α,β-acetylenic esters were obtained in excellent enantiomeric excesses (up to 94% ee) under optimized conditions. Crown Copyright
