Enantioselective (formal) aza-Diels-Alder reactions with non-Danishefsky-type dienes.
نویسندگان
چکیده
Enantioselective (formal) aza-Diels-Alder reactions between acylhydrazones and non-Danishefsky-type dienes have been developed. The reactions are promoted by a simple and economical chiral silicon Lewis acid and are typically conducted at ambient temperature. Both glyoxylate- and aliphatic aldehyde-derived hydrazones may be employed, as may variously substituted dienes, leading to the synthesis of a diverse array of tetrahydropyridines with good to excellent levels of enantioselectivity.
منابع مشابه
1-Nitronaphtalene as a Dienophile in Diels-Alder Reactions
the utilization of substitued dienes with electron-donor groups and under high pressure conditions, induces the dienophilic character of 1-nitronaphtalene in Diels-Alder reactions, giving the products with and without the nitro-group, the yield depending on the nature of the dienes substituent groups. Introduction The Diels-Alder reaction has been subject of extensive studies for both theoretic...
متن کاملAsymmetric Diels-Alder reactions catalyzed by a triflic acid activated chiral oxazaborolidine.
This paper reports a new method for the generation of chiral Lewis superacids by protonation of a non-Lewis acidic oxazaborolidine (1) with triflic acid. The resulting cationic species (3) are powerful and highly enantioselective catalysts for the Diels-Alder reaction of various 1,3-dienes with alpha,beta-enals. An optimization study (see Table 1) led to the selection of reaction conditions and...
متن کاملIntramolecular Diels–Alder Reactions of Cycloalkenones: Stereoselectivity, Lewis Acid Acceleration, and Halogen Substituent Effects
The intramolecular Diels-Alder reactions of cycloalkenones and terminal dienes occur with high endo stereoselectivity, both thermally and under Lewis-acidic conditions. Through computations, we show that steric repulsion and tether conformation govern the selectivity of the reaction, and incorporation of either BF3 or α-halogenation increases the rate of cycloaddition. With a longer tether, iso...
متن کاملEnantioselective rare-earth catalyzed quinone Diels-Alder reactions.
A highly enantioselective, quinone Diels-Alder reaction catalyzed by chiral samarium and gadolinium pyridyl-bis(oxazoline) (pybox) complexes has been developed. The reaction scope has been extended to include three quinones and five dienes, all of which exclusively provide the expected endo product in excellent yields and enantioselectivities.
متن کاملEnantioselective construction of lactone[2,3-b]piperidine skeletons via organocatalytic tandem reactions.
A highly enantioselective construction of delta- and gamma-lactone[2,3-b]piperidine skeletons was accomplished by tandem aza-Diels-Alder reaction-hemiacetal formation-oxidation from N-Tos-1-aza-1,3-butadienes and aliphatic dialdehydes.
متن کاملذخیره 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 ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Journal of the American Chemical Society
دوره 132 30 شماره
صفحات -
تاریخ انتشار 2010