Diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams

نویسنده

  • Katherine M Byrd
چکیده

The conjugate addition reaction has been a useful tool in the formation of carbon-carbon bonds. The utility of this reaction has been demonstrated in the synthesis of many natural products, materials, and pharmacological agents. In the last three decades, there has been a significant increase in the development of asymmetric variants of this reaction. Unfortunately, conjugate addition reactions using α,β-unsaturated amides and lactams remain underdeveloped due to their inherently low reactivity. This review highlights the work that has been done on both diastereoselective and enantioselective conjugate addition reactions utilizing α,β-unsaturated amides and lactams.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

A Highly Diastereoselective and Enantioselective Phase-Transfer Catalyzed Epoxidation of β-Trifluoromethyl-β,β-disubstituted Enones with H2O2

Trifluoromethylated organic compounds, especially chiral quaternary alcohols bearing trifluoromethyl group are of important intermediates in drugs, agrochemicals and etc.An efficient epoxidation of β-CF3-β,β-disubstituted unsaturated ketones (6) has been developed with environmental benign hydrogen peroxide as the oxidant and F5-substituted chiral qua...

متن کامل

Asymmetric Organocatalytic Reactions of α, β-Unsaturated Cyclic Ketones

The 1,4-conjugate addition of nucleophiles to α,β-unsaturated carbonyl compounds represents one fundamental bond-forming reaction in organic synthesis. The development of effective organocatalysts for the enantioselective conjugate addition of malonate, nitroalkane and other carbon and heteroatom nucleophiles to cycloenones constitutes an important research field and has been explored in recent...

متن کامل

Cu(II)-catalyzed asymmetric boron conjugate addition to α,β-unsaturated imines in water.

Enantioselective conjugate addition of bis(pinacolato)diboron to α,β-unsaturated imines proceeds smoothly in water in the presence of a chiral copper(II) complex consisting of Cu(OAc)2 and chiral 2,2'-bipyridine. The corresponding β-boryl imines, which were oxidized to β-hydroxy imines, further leading to γ-amino alcohols, were obtained in high yields and high enantioselectivities.

متن کامل

NHC-mediated enantioselective formal [4 + 2] cycloadditions of alkylarylketenes and β,γ-unsaturated α-ketocarboxylic esters and amides.

Chiral N-heterocyclic carbenes (NHCs) promote the asymmetric formal [4 + 2] cycloaddition of alkylarylketenes with β,γ-unsaturated α-ketocarboxylic esters and amides. Divergent diastereoselectivity is observed in this process, with γ-aryl-β,γ-unsaturated α-ketocarboxylic esters and amides giving preferentially syn-dihydropyranones (up to 68 : 32 dr syn : anti, up to 98% ee), while γ-alkyl-deriv...

متن کامل

Organocatalytic tandem Michael addition reactions: A powerful access to the enantioselective synthesis of functionalized chromenes, thiochromenes and 1,2-dihydroquinolines

Enantioselective organocatalysis has become a field of central importance within asymmetric chemical synthesis and appears to be efficient approach toward the construction of complex chiral molecules from simple achiral materials in one-pot transformations under mild conditions with high stereocontrol. This review addresses the most significant synthetic methods reported on chiral-amine-catalyz...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره 11  شماره 

صفحات  -

تاریخ انتشار 2015