220006-54-2Relevant academic research and scientific papers
Palladium-Catalyzed Enantioselective Heteroarenyne Cycloisomerization Reaction
Liang, Ren-Xiao,Song, Ling-Jie,Lu, Jin-Bo,Xu, Wei-Yan,Ding, Chao,Jia, Yi-Xia
, p. 7412 - 7417 (2021)
The extensively developed ene-type enantioselective cycloisomerization of classical 1,n-enynes provides an efficient approach to chiral cyclic 1,4-dienes. In contrast, the catalytic asymmetric heteroarenyne (heteroarene–alkyne) cycloisomerization involving the dearomative transformation of endocyclic aromatic C=C bonds remains unknown. Herein, we communicate a PdH-catalyzed enantioselective heteroarenyne cycloisomerization reaction of alkyne-tethered indole substrates (formal 1,5- and 1,6-enynes). Based on this strategy, a variety of structurally diverse chiral spiro and fused indoline derivatives bearing quaternary stereocenters and exocyclic C=C bonds are afforded in moderate to excellent yields and excellent enantioselectivities (up to 98 % ee). The classical ene-type enantioselective 1,5-enyne cycloisomerization of N-vinylpropiolamides is also developed to afford chiral 2-pyrrolones in good to excellent ee values.
A one-pot synthesis and functionalization of polyynes
Morisaki, Yasuhiro,Luu, Thanh,Tykwinski, Rik R.
, p. 689 - 692 (2007/10/03)
A one-pot synthesis and derivatization of diynes and triynes is reported. The polyyne framework is formed from a dibromoolefin precursor based on a carbenoid rearrangement, and the resulting Li-acetylide is then trapped in situ with an electrophile to pro
Rapid synthesis of α,β-didehydroaspartic-acid derivatives carrying a β-substituent
Schottelius, Marc J.,Chen, Peter
, p. 2341 - 2347 (2007/10/03)
A convenient preparation of N-(alkoxycarbonyl)-2,3-didehydroaspartic acid anhydrides 4 with substitution at the 3-position is reported. The key step is a cobalt-mediated acylation of an acetylene moiety, producing the highly functionalized didehydroamine
