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1‐Alkoxyamino‐2‐nitroalkanes as Key Building Blocks for a Chemo‐ and Diastereoselective Synthesis of a New Type of Polyfunctionalized N ‐Alkoxypiperidine
Author(s) -
LópezGarcía M. Ángeles,
Maya Inés,
FernándezBolaños José G.,
Bosica Giovanna,
Ballini Roberto
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000540
Subject(s) - chemistry , stereocenter , alkoxy group , michael reaction , conjugate , diastereomer , intramolecular force , adduct , stereochemistry , combinatorial chemistry , enantioselective synthesis , organic chemistry , catalysis , mathematical analysis , alkyl , mathematics
A highly efficient conversion of β‐nitrostyrenes into a new kind of functionalized N ‐alkoxy‐2‐hydroxypiperidine in two steps was developed, giving excellent yields and diastereoselectivity. The prepared compounds are the first examples of N ‐alkoxy‐2‐hydroxypiperidines. The synthetic approach involved the conjugate addition of alkoxyamines to β‐nitrostyrenes, followed by Michael addition of the isolated nitroalkoxyamines to α,β‐unsaturated carbonyl compounds, and intramolecular addition of the alkoxyamino group to the carbonyl functionality of the (non‐isolated) adducts. Although three stereogenic centers are formed, only one diastereoisomer was detected. This unprecedented sequence of reactions can also be performed in a one‐pot fashion.