Premium
In Situ Generation of Chiral N ‐Dienyl Lactams in a Multicomponent Reaction: An Efficient and Highly Selective Way to Asymmetric Amidocyclohexenes
Author(s) -
Hübner Sandra,
Jiao Haijun,
Michalik Dirk,
Neumann Helfried,
Klaus Stefan,
Strübing Dirk,
Spannenberg Anke,
Beller Matthias
Publication year - 2007
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.200600428
Subject(s) - in situ , combinatorial chemistry , chemistry , stereochemistry , organic chemistry
Chiral N ‐dienyl lactams are crucial building blocks for the synthesis of complex organic compounds. However, their generation is rather challenging. This paper reports on a highly efficient and diastereoselective multicomponent methodology utilizing chiral a mides, a ldehydes, and d ienophiles (AAD reaction). The three components readily react under in situ generation of chiral N ‐dienyl lactams which undergo a subsequent Diels–Alder reaction. Different chiral amides have been employed in the standard protocol delivering yields up to 94 %, and selectivities up to 90 % de . Moreover, DFT calculations were performed to explain the obtained selectivities.