TY - JOUR
T1 - Copper-catalyzed γ-selective and stereospecific direct allylic alkylation of terminal alkynes
T2 - Synthesis of skipped enynes
AU - Makida, Yusuke
AU - Takayama, Yurie
AU - Ohmiya, Hirohisa
AU - Sawamura, Masaya
N1 - Copyright:
Copyright 2013 Elsevier B.V., All rights reserved.
PY - 2013/5/10
Y1 - 2013/5/10
N2 - Skipping out: The title reaction using internal secondary allylic phosphates proceeded with excellent γ regioselectivity and E stereoselectivity to give skipped enynes. Enantioenriched secondary allylic phosphates proceeded with 1,3-anti stereochemistry to afford the corresponding chiral 1,4-enynes, which were used for various derivatizations and the formal total synthesis of a GnRH antagonist. phen=1,10-phenanthroline.
AB - Skipping out: The title reaction using internal secondary allylic phosphates proceeded with excellent γ regioselectivity and E stereoselectivity to give skipped enynes. Enantioenriched secondary allylic phosphates proceeded with 1,3-anti stereochemistry to afford the corresponding chiral 1,4-enynes, which were used for various derivatizations and the formal total synthesis of a GnRH antagonist. phen=1,10-phenanthroline.
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U2 - 10.1002/anie.201300785
DO - 10.1002/anie.201300785
M3 - Article
C2 - 23576405
AN - SCOPUS:84877282172
SN - 1433-7851
VL - 52
SP - 5350
EP - 5354
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 20
ER -