100372-86-9Relevant academic research and scientific papers
Reductive Alkylation of Tertiary Lactams via Addition of Organocopper (RCu) Reagents to Thioiminium Ions
Mateo, Pierre,Cinqualbre, Joséphine E.,Meyer Mojzes, Melinda,Schenk, Kurt,Renaud, Philippe
supporting information, p. 12318 - 12327 (2017/12/08)
A simple procedure for the conversion of tertiary lactams to 2-monoalkylated cyclic amines is described. The reaction sequence involves conversion of a lactam to a thioiminium ion followed by reaction with an organocopper (RCu) reagent and final reduction with triacetoxyborohydride. The reaction is high yielding and shows an excellent functional group tolerance. Its utility is demonstrated by a rapid synthesis of indolizidine 167B. The excellent chemoselectivity of the process, where only monoalkylation products are formed, is rationalized by a mechanism involving the formation of a transient enamine.
Chemoenzymatic enantioselective synthesis of 3-hydroxy-2-pyrrolidinones and 3-hydroxy-2-piperidinones
Kamal, Ahmed,Ramana, K. Venkata,Ramana, A. Venkata,Babu, A. Hari
, p. 2587 - 2594 (2007/10/03)
The enantioselective synthesis of 3-hydroxypyrrolidin-2-ones and 3-hydroxy piperidin-2-ones has been carried out in high enantiomeric excess employing immobilized lipase from Pseudomonas cepacia.
