منابع مشابه
β-Amino functionalization of cinnamic Weinreb amides in ionic liquid
2-Ns-Protected β-amino Weinreb amides were synthesized by aminochlorination of α,β-unsaturated Weinreb amides in an ionic liquid, 1-n-butyl-3-methylimidazolium bis(trifluoromethanesulfonyl)imide ([BMIM][NTf2]). Processed without the use of metal catalysts or the need of an inert gas atmosphere, the presented process can be readily performed as a one-pot synthesis at room temperature. Moreover, ...
متن کاملChemoselective efficient synthesis of functionalized β-oxonitriles through cyanomethylation of Weinreb amides.
A synthesis of β-oxonitriles is reported via the generation of R(1)R(2)CLiCN species followed by the trapping with variously decorated Weinreb amides. The optimization study revealed that lithiation of acetonitriles is best accomplished by deprotonation with MeLi-LiBr at low temperature. The protocol can be conveniently adapted to the synthesis of α-mono or α,α-disubstituted cyanoketones. (15)N...
متن کاملReductive hydroxyalkylation/alkylation of amines with lactones/esters.
We have developed a one-pot method for the direct intermolecular reductive hydroxyalkylation or alkylation of amines using lactones or esters as the hydroxyalkylating/alkylating reagents. The method is based on the in situ amidation of lactones/esters with DIBAL-H-amine complex (for primary amines) or DIBAL-H-amine hydrochloride salt complex (for secondary amines), followed by reduction of the ...
متن کاملMechanism of acylation of lithium phenylacetylide with a Weinreb amide.
Additions of lithium phenylacetylide to a Weinreb amide are described. Dimeric lithium acetylide reacts via a monosolvated monomer-based transition structure. The robust tetrahedral intermediate forms sequentially a C(1) 2:2 mixed tetramer with the excess lithium acetylide and a 1:3 (alkoxide-rich) mixed tetramer. The stabilities of the mixed tetramers are consistent with a pronounced autoinhib...
متن کاملMethodology for in situ protection of aldehydes and ketones using trimethylsilyl trifluoromethanesulfonate and phosphines: selective alkylation and reduction of ketones, esters, amides, and nitriles.
A methodology for selective transformations of ketones, esters, Weinreb amides, and nitriles in the presence of aldehydes has been developed. The use of a combination of PPh(3)-trimethylsilyl trifluoromethanesulfonate (TMSOTf) promotes selective transformation of aldehydes to their corresponding, temporarily protected, O,P-acetal type phosphonium salts. Because, hydrolytic work-up following ens...
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ژورنال
عنوان ژورنال: Synlett
سال: 2015
ISSN: 0936-5214,1437-2096
DOI: 10.1055/s-0034-1380055