TY - JOUR
T1 - Recent advances in the Overman rearrangement
T2 - Synthesis of natural products and valuable compounds
AU - Fernandes, Rodney A.
AU - Kattanguru, Pullaiah
AU - Gholap, Sachin P.
AU - Chaudhari, Dipali A.
N1 - Publisher Copyright:
© 2017 The Royal Society of Chemistry.
PY - 2017
Y1 - 2017
N2 - In the past decade, the Overman rearrangement, an important C-N bond forming reaction, has been intensely used in the synthesis of natural products, synthetic intermediates, building blocks and valuable compounds. This review documents the reports on this rearrangement reaction since 2005. The reaction has been tactfully used to introduce amine functionality in the synthesis of natural products. It is a one-pot process using the intermediate imidate which upon rearrangement generates the amide that can be hydrolysed to the amine. The method has tremendous potential for rapid modification of various amino compounds and can be combined with other Claisen-rearrangements or other reactions for one-pot processes for further exploration.
AB - In the past decade, the Overman rearrangement, an important C-N bond forming reaction, has been intensely used in the synthesis of natural products, synthetic intermediates, building blocks and valuable compounds. This review documents the reports on this rearrangement reaction since 2005. The reaction has been tactfully used to introduce amine functionality in the synthesis of natural products. It is a one-pot process using the intermediate imidate which upon rearrangement generates the amide that can be hydrolysed to the amine. The method has tremendous potential for rapid modification of various amino compounds and can be combined with other Claisen-rearrangements or other reactions for one-pot processes for further exploration.
UR - http://www.scopus.com/inward/record.url?scp=85016417494&partnerID=8YFLogxK
U2 - 10.1039/c6ob02625g
DO - 10.1039/c6ob02625g
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C2 - 28272639
AN - SCOPUS:85016417494
SN - 1477-0520
VL - 15
SP - 2672
EP - 2710
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 13
ER -