Synthesis of achiral and chiral N-protected γ-amino-β-ketones and β-ketoesters
نویسندگان
چکیده
منابع مشابه
Efficient synthesis of β’-amino-α,β-unsaturated ketones
A general and simple procedure to access chiral β'-amino-α,β-enones, in seven steps, from an α,β unsaturated ester has been described. The use of a Horner-Wadsworth-Emmons reaction as a key step for generating the β'-amino-α,β-enones, permits access to a range of substrates under mild conditions and in moderate to high yield.
متن کاملTin(II) chloride assisted synthesis of N-protected γ-amino β-keto esters through semipinacol rearrangement.
A facile synthetic route for the preparation of N-protected γ-amino β-keto esters from amino aldehydes and ethyl diazoacetate is described. The two component coupling is facilitated by tin(II) chloride followed by semipinacol rearrangement leading to the product in quantitative yield. The reaction is mild, instantaneous and compatible with Boc-, Fmoc- and Cbz-amino protecting groups.
متن کاملAsymmetric organocatalytic decarboxylative Mannich reaction using β-keto acids: A new protocol for the synthesis of chiral β-amino ketones
The first decarboxylative Mannich reaction employing β-keto acids, catalyzed by cinchonine-derived bifunctional thiourea catalyst has been described. The desired β-amino ketones were obtained in excellent yields and with moderate to good enantioselectivities.
متن کاملAsymmetric anti-aldol addition of achiral ketones via chiral N-amino cyclic carbamate hydrazones.
The asymmetric anti-aldol addition of ketone-derived donors and aldehyde acceptors is described. Asymmetric induction is achieved through the use of chiral N-amino cyclic carbamate (ACC) auxiliaries. The transformation exhibits essentially perfect anti-diastereoselectivity and enantioselectivity, and has the unusual feature of proceeding via thermodynamic, rather than kinetic control.
متن کاملSynthesis of Novel Sterically Demanding Carbo- and Heterocyclic β-Ketoesters
We present an easy method for the synthesis of β-ketoesters starting from various carbocyclic and heterocyclic carboxylic acids and esters. The β-ketoester side-chain was introduced by a sequence involving α-deprotonation and quenching with CO2, conversion to the corresponding acid chloride and subsequent chain elongation using deprotonated ethyl acetate.
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: Arkivoc
سال: 2007
ISSN: 1551-7012
DOI: 10.3998/ark.5550190.0009.a04