Double Addition of Propargylzinc Reagents to Acylcyanohydrins and Cyanocarbonates
نویسندگان
چکیده
Two darts in the middle! This work reports double addition of propargylzinc reagents to nitriles (acylcyanohydrins and cyanocarbonates). methodology provides a straightforward access dipropargylic α,α-disubstituted hydroxyamides or N-Boc-protected amino alcohols which can be converted into functionalized pyridine derivatives after cobalt-catalyzed [2+2+2] cycloaddition reactions involving nitriles.
منابع مشابه
Enantioselective Addition of Grignard Reagents to Aldehydes
The addition of Grignard reagents to aldehydes in the presence of chiral aminoalcohols shows a moderate enantioselectivity. The study carried out with a series of ligands allows the correlation between the structural characteristics and their reactivity. Introduction The use of chiral aminoalcohol to lead asymmetrically nucleophilic additions of organometallics to carbonyl compounds is a field ...
متن کاملCatalytic asymmetric conjugate addition of Grignard reagents to chromones.
A highly regio- and enantioselective copper catalysed direct conjugate addition of Grignard reagents to chromones has been developed taking advantage of the reduced reactivity of the resulting magnesium enolates. This methodology tolerates a broad scope of alkyl Grignards including secondary alkyl magnesium reagents as well as functionalised chromones.
متن کاملAsymmetric conjugate addition of Grignard reagents to pyranones.
An efficient enantioselective synthesis of lactones was developed based on the catalytic asymmetric conjugate addition (ACA) of alkyl Grignard reagents to pyranones. The use of 2H-pyran-2-one for the first time in the ACA with Grignard reagents allows for a variety of further transformations to access highly versatile building blocks such as β-alkyl substituted aldehydes or β-bromo-γ-alkyl subs...
متن کاملEnantioselective addition of organozinc reagents to carbonyl compounds*
Different chiral camphorsulfonamide derivatives containing a hydroxy or a sulfonamido functionality, as well as chiral 1,2-hydroxysulfonamides, have been evaluated as chiral promoters in the classical enantioselective addition of dialkylzinc reagents to aldehydes in the presence of titanium tetraisopropoxide (ee up to 96 %). Surprisingly, ligands with a structure of isoborneol are able to promo...
متن کاملCatalytic enantioselective addition of Grignard reagents to aromatic silyl ketimines
α-Chiral amines are of significant importance in medicinal chemistry, asymmetric synthesis and material science, but methods for their efficient synthesis are scarce. In particular, the synthesis of α-chiral amines with the challenging tetrasubstituted carbon stereocentre is a long-standing problem and catalytic asymmetric additions of organometallic reagents to ketimines that would give direct...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: European Journal of Organic Chemistry
سال: 2022
ISSN: ['1434-193X', '1099-0690']
DOI: https://doi.org/10.1002/ejoc.202200891