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Enantioselective Synthesis of P‐Stereogenic Alkynylphosphine Oxides by Rh‐Catalyzed [2+2+2] Cycloaddition
Author(s) -
Nishida Goushi,
Noguchi Keiichi,
Hirano Masao,
Tanaka Ken
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.200800144
Subject(s) - stereocenter , enantioselective synthesis , rhodium , cycloaddition , sulfonamide , cationic polymerization , catalysis , chemistry , stereochemistry , medicinal chemistry , organic chemistry
Two plus two plus two : An enantioselective synthesis of P‐stereogenic alkynylphosphine oxides through a cationic rhodium(I)/modified‐binap complex catalyzed [2+2+2] cycloaddition of symmetrical dialkynylphosphine oxides with 1,6‐diynes was developed (see scheme; binap=2,2′‐bis(diphenylphosphanyl)‐1,1′‐binaphthyl, Z=CH 2 , O, or N ‐sulfonamide). Furthermore, this method permits the synthesis of a C 2 ‐symmetric P‐stereogenic bis(alkynylphosphine oxide).