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Organocatalytic Asymmetric α‐Aminoxylation/Aza‐Michael Reactions for the Synthesis of Functionalized Tetrahydro‐1,2‐oxazines
Author(s) -
Lu Min,
Zhu Di,
Lu Yunpeng,
Hou Yuxuan,
Tan Bin,
Zhong Guofu
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200803731
Subject(s) - stereocenter , oxazines , hydrogen bond , yield (engineering) , chemistry , catalysis , molecule , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , materials science , metallurgy
Catalyst for THOught : The title reaction using acyclic nitroalkenals for the asymmetric installation of both CO and CN bonds led to functionalized tetrahydro‐1,2‐oxazines (THOs) having up to three stereogenic centers; the products were isolated in up to 90 % yield with excellent enantioselectivity and complete diastereoselectivity (see scheme). DFT calculations reveal an unprecedented transition state containing a molecule of water, which assists in the CN bond‐forming step by participating in two hydrogen bonds.