180516-67-0Relevant academic research and scientific papers
A general synthesis of pyrroles and fused pyrrole systems from ketones and amino acids
Nagafuji, Pamela,Cushman, Mark
, p. 4999 - 5003 (1996)
The lithium enolates of ketones react with BOC-α-amino aldehydes and BOC-α-amino ketones to afford aldol intermediates that cyclize under acidic conditions to yield pyrroles. The BOC-amino aldehydes and ketones are readily available from α-amino acids. The method allows incorporation of a wide variety of substituents at any of the five atoms of the pyrrole ring and is also suitable for the preparation of fused pyrrole systems.
An efficient procedure for the synthesis of 2-N-Boc-amino-3,5-diols
Dias, Luiz C.,Fattori, Juliana,Perez, Carla C.,de Oliveira, Vanda M.,Aguilar, Andrea M.
, p. 5891 - 5903 (2008/12/22)
We wish to describe here the diastereoselective reaction between chiral N-Boc-α-amino aldehydes with both achiral allyltrichlorostannanes leading to 1,2-syn-N-Boc-α-amino alcohols, which are easily converted to the corresponding 4-N-Boc-amino-3-hydroxy ketones after treatment with catalytic amounts of OsO4 in the presence of NaIO4. After reduction of the carbonyl function, these 4-N-Boc-amino-3-hydroxy ketones were converted to 1-deoxy-5-hydroxy sphingosine analogues.
A facile access to pyrroles from amino acids via an aza-Wacker cyclization
Zhang, Zuhui,Zhang, Jintang,Tan, Jiajing,Wang, Zhiyong
, p. 5180 - 5182 (2008/12/20)
(Chemical Equation Presented) A facile and efficient synthesis of pyrroles from readily available amino acids is described. The key step in the method is an aza-Wacker oxidative cyclization catalyzed by palladium(II)/Cu(OTf) 2. A series of pyrroles were obtained by this method under mild conditions.
A facile synthesis of N-Boc-protected pyrroles by cyclodehydration of γ-amino-α,β-enals and -enones
Paulus, Olivier,Alcaraz, Gilles,Vaultier, Michel
, p. 2565 - 2572 (2007/10/03)
A novel series of N-Boc-substituted and fused pyrroles was prepared by cyclodehydration of readily accessible (E)-γ-(tert-butoxycarbonylamino)-α,β-enals and -enones. Functionalisation of the pyrrole ring was then explored with 2-borylated pyrroles in the Suzuki-Miyaura coupling. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.
