1492959-96-2Relevant academic research and scientific papers
Investigation of cationic Claisen-type electrophilic rearrangements of amides
Padmanaban, Mohan,Carvalho, Luísa C.R.,Petkova, Desislava,Lee, Ji-Woong,Santos, A. Sofia,Marques, M. Manuel B.,Maulide, Nuno
supporting information, p. 5994 - 6005 (2015/08/03)
Abstract Herein we report an extension of the electrophilic rearrangement of amides to the preparation of α-prenyl-hydrocoumarins, indoles, isoquinolines and dihydro-isoquinolinones. An unusual competitive sulfonyl migration, uncovered upon attempted aza-
Amides in one pot from Carboxylic Acids and Amines via Sulfinylamides
Bai, Jianfei,Zambron, Bartosz K.,Vogel, Pierre
supporting information, p. 604 - 607 (2014/04/03)
An efficient method has been developed for the direct amidification of carboxylic acids via sulfinylamides preformed in situ by the reaction of pure amines with prop-2- ene-1-sulfinyl chloride. The method can be applied to aliphatic acids, including pivalic acid, aromatic acids, and primary and secondary amines. It is compatible with acids bearing unprotected alcohol, phenol, and ketone moieties and applicable to the synthesis of peptides. It does not induce their a-epimerization.
Developing the scope of o→c aryl migrations: Exploring amide substrates as potential precursors for asymmetric reactions
Ameen, Dana,Snape, Timothy J.
, p. 1925 - 1934 (2014/04/03)
A new and mild method for the production of diasteromerically enriched α-aryl carbonyl compounds has been achieved. Although only modest diastereoselectivies are observed, they demonstrate the potential of the method for further optimisation. It also appears that reactions that proceed through a five-membered spirocyclic transition state rearrange, whereas those proceeding through a six-membered transition state do not, but stop at the diaryl ether stage.
Developing the Scope of O→C Aryl Migrations: Exploring Amide Substrates as Potential Precursors for Asymmetric Reactions
Ameen, Dana,Snape, Timothy J.
, p. 1925 - 1934 (2015/10/05)
A new and mild method for the production of diasteromerically enriched α-aryl carbonyl compounds has been achieved. Although only modest diastereoselectivies are observed, they demonstrate the potential of the method for further optimisation. It also appears that reactions that proceed through a five-membered spirocyclic transition state rearrange, whereas those proceeding through a six-membered transition state do not, but stop at the diaryl ether stage. A mild O→C aryl migration (Truce-Smiles rearrangement reaction) has been expanded to include amides as precursors, and it has been shown that the product ratios are dependent on the structure of the starting amides. Chiral auxiliaries have been incorporated in attempts to make the rearrangement asymmetric and modest diastereoselectivities were obtained.
