In one embodiment, the present application discloses mixtures comprising (a) water in an amount of at least 1% wt/wt of the mixture; (b) a transition metal catalyst; and (c) one or more solubilizing agents; and methods for using such mixtures for performing transition metal mediated bond formation reactions.
Reaction of arylboronreagents, arylboronic acids or arylborates, which are readily accessible by lithiation of aryl bromides followed by treatment with trimethoxyborane, with α,β-unsaturated esters in the presence of rhodium/(S)-binap catalyst proceeded with high enantioselectivity to give high yields of optically active β-aryl esters of up to 98% ee. The enantioselectivity depends on the steric bulkiness
Highly (<i>E</i>)-Selective Wadsworth−Emmons Reactions Promoted by Methylmagnesium Bromide
作者:Timothy D. W. Claridge、Stephen G. Davies、James A. Lee、Rebecca L. Nicholson、Paul M. Roberts、Angela J. Russell、Andrew D. Smith、Steven M. Toms
DOI:10.1021/ol802212e
日期:2008.12.4
An experimentally simple protocol for the very highly (E)-selective Wadsworth-Emmonsreaction [(E):(Z) selectivities in excess of 180:1 in some cases] of a range of straight-chain and branched aliphatic, substituted aromatic, and base-sensitive aldehydes via reaction with an alkyl diethylphosphonoacetate and MeMgBr is reported.
Racemic N-sulfonyloxaziridines as highly diastereoselective enolate hydroxylating agents: enantioselective synthesis of (2S,3S)-3-amino-N-cyclopropyl-2-hydroxyhexanamide
作者:Eleonóra Kiss、István E. Markó、Michel Guillaume
DOI:10.1016/j.tet.2011.09.090
日期:2011.11
by hydroxylation of the in situ generated β-amino enolate was employed for the formation of the required stereogenic centres. Importantly, very high diastereoselectivities can still be achieved in the key-step when the relatively expensive and enantiopure (camphorsulfonyl)oxaziridine hydroxylating agent is replaced by racemic trans-N-sulfonyloxaziridines. Among the tested N-sulfonyloxaziridines the