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The Catalytic Asymmetric Diels–Alder Reactions and Post‐cycloaddition Reductive Transpositions of 1‐Hydrazinodienes
Author(s) -
Xie Hao,
Sammis Glenn M.,
Flamme Eric M.,
Kraml Christina M.,
Sorensen Erik J.
Publication year - 2011
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102394
Subject(s) - allylic rearrangement , cycloaddition , construct (python library) , catalysis , alder , stereoselectivity , chemistry , computer science , organic chemistry , botany , biology , programming language
Cycling through : Type I cyclohexenes are produced with high margins of stereoselectivity by chiral, catalyst‐controlled, Diels–Alder reactions between 1‐hydrazinodienes and N ‐acryloyl oxazolidinone dienophiles, and readily transformed to cyclohexenes III via a putative, transient allylic diazene II (see scheme). This chemistry gives access to functionalized cyclohexenes that can be difficult to construct by alternative methods.