Stereoselective Synthesis of Vinyl Ethers by the Reaction of N-(Arylidene(or alkylidene)amino)-2-azetidinones with Ozone
摘要:
Ozonolysis of N-(arylidene(or alkylidene)amino)-2-azetidinones followed by NaBH4 workup yields enol ethers in good yields with high levels of stereoselectivity. Di- and trisubstituted olefin derivatives are available through this procedure. Chiral 2-azetidinones lead to enol ethers with a chiral moiety without racemization. The reaction is thought to occur through a novel B-type fragmentation of the 2-azetidinone ring. This process is closely related to the well-known N-nitrosoamide to ester rearrangement and the decarboxylation of oxetan-2-ones.
Combinatorial preparation of a substance library with removal of a zwitterionic compound by precipitation
申请人:——
公开号:US20020037534A1
公开(公告)日:2002-03-28
A process for the combinatorial preparation of a substance library from n different compounds in an array of n different reaction solutions at n spatially separate reaction sites, in which at each of the n reaction sites
(a) from in each case m reactants, in one reaction or reaction sequence, a zwitterionic compound is obtained dissolved in a polar solvent,
(b) the zwitterionic compound is precipitated as a solid by addition of a nonpolar solvent, isolated and then obtained in pure form,
(c) if appropriate the zwitterionic compound is further reacted, with each of the n reaction solutions differing from each of the n−1 other reaction solutions in at least one of the m reactants,
is described.
Kombinatorische Herstellung einer Substanzbibliothek unter Abtrennung einer zwitterionischen Verbindung durch Fällung
申请人:BASF AKTIENGESELLSCHAFT
公开号:EP1188732A2
公开(公告)日:2002-03-20
Verfahren zur kombinatorischen Herstellung einer Substanzbibliothek aus n verschiedenen Verbindungen in einem Array aus n verschiedenen Reaktionsansätzen an n räumlich getrennten Reaktionsorten, bei dem an jedem der n Reaktionsorte
a) aus jeweils m Reaktanten in einer Reaktion oder Reaktionssequenz eine zwitterionische Verbindung in einem polaren Lösungsmittel gelöst erhalten wird,
b) die zwitterionische Verbindung durch Zugabe eine unpolaren Lösungsmittels als Feststoff gefällt, isoliert und damit in reiner Form erhalten wird,
c) gegebenenfalls die zwitterionische Verbindung weiter umgesetzt wird, wobei sich jeder der n Reaktionsansätze von jedem der n - 1 übrigen Reaktionsansätzen in mindestens einem der m Reaktanten unterscheidet.
用 n 种不同的化合物组合制备物质库的工艺,在 n 个空间上分开的反应点上进行 n 种不同的反应制备,其中在 n 个反应点中的每个反应点上
a) 在每个反应或反应序列中,从 m 个反应物中得到一个溶解在极性溶剂中的齐聚物、
b) 加入非极性溶剂,将该齐聚物沉淀为固体,并分离出来,得到纯净的齐聚物、
c) 如果需要,进一步反应该齐聚物,其中 n 个反应批次中的每个反应批次与 n - 1 个剩余反应批次中的每个反应批次在 m 个反应物中至少有一个反应物不同。
Stereoselective Synthesis of Vinyl Ethers by the Reaction of N-(Arylidene(or alkylidene)amino)-2-azetidinones with Ozone
作者:Benito Alcaide、Javier Perez-Castells、Concepcion Polanco、Miguel A. Sierra
DOI:10.1021/jo00124a008
日期:1995.9
Ozonolysis of N-(arylidene(or alkylidene)amino)-2-azetidinones followed by NaBH4 workup yields enol ethers in good yields with high levels of stereoselectivity. Di- and trisubstituted olefin derivatives are available through this procedure. Chiral 2-azetidinones lead to enol ethers with a chiral moiety without racemization. The reaction is thought to occur through a novel B-type fragmentation of the 2-azetidinone ring. This process is closely related to the well-known N-nitrosoamide to ester rearrangement and the decarboxylation of oxetan-2-ones.
Gibson, Susan E.; Ham, Peter; Jefferson, Gary R., Chemical Communications, 1998, # 1, p. 123 - 124