Organocatalytic Synthesis of α-Trifluoromethyl Allylboronic Acids by Enantioselective 1,2-Borotropic Migration
نویسندگان
چکیده
منابع مشابه
Organocatalytic, enantioselective synthesis of benzoxaboroles via Wittig/oxa-Michael reaction Cascade of α-formyl boronic acids.
An unprecedented enantioselective synthesis of 3-substituted benzoxaboroles has been developed. An in situ generated ortho-boronic acid containing chalcone provides the chiral benzoxaboroles via an asymmetric oxa-Michael addition of hydroxyl group attached to the boronic acid triggered by the cinchona alkaloid based chiral amino-squaramide catalysts. In general, good yields with good to excelle...
متن کاملA concise organocatalytic and enantioselective synthesis of isotetronic acids.
A concise enantioselective route to isotetronic acids using an organocatalyzed aldol reaction between alpha-oxocarboxylic acids and aldehydes has been developed, leading to the titled compounds in reasonable yields and good enantioselectivities.
متن کاملEnantioselective organocatalytic α-fluorination of cyclic ketones.
The first highly enantioselective α-fluorination of ketones using organocatalysis has been accomplished. The long-standing problem of enantioselective ketone α-fluorination via enamine activation has been overcome via high-throughput evaluation of a new library of amine catalysts. The optimal system, a primary amine functionalized Cinchona alkaloid, allows the direct and asymmetric α-fluorinati...
متن کاملEnantioselective organocatalytic Hantzsch synthesis of polyhydroquinolines.
The four-component Hantzsch reaction provides access to pharmaceutically important dihydropyridines. To expand the utility of this method, we have developed a route under organocatalytic conditions with good yields and excellent ee's. Through catalyst screening, we found that a BINOL-phosphoric acid allowed enantioselective synthesis of six-membered heterocycles with a variety of substitution p...
متن کاملOrganocatalytic enantioselective synthesis of 2,3-dihydropyridazines.
We have developed an efficient procedure for the easy and straightforward preparation of functionalized dihydropyridazines as highly enantiopure materials by reaction of pyruvaldehyde 2-tosyl hydrazone with a variety of α,β-unsaturated aldehydes using a chiral secondary amine as catalyst. The overall process consists of a cascade reaction involving an initial aza-Michael reaction, in which the ...
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: Journal of the American Chemical Society
سال: 2020
ISSN: 0002-7863,1520-5126
DOI: 10.1021/jacs.0c09923