Matches in SemOpenAlex for { <https://semopenalex.org/work/W2026421941> ?p ?o ?g. }
- W2026421941 endingPage "10608" @default.
- W2026421941 startingPage "10592" @default.
- W2026421941 abstract "The scope and limitations of the copper-catalyzed propargylic amination of various propargylic esters with amines are presented, where optically active diphosphines such as Cl-MeO-BIPHEP and BINAP work as good chiral ligands. A variety of secondary amines are available as nucleophiles for this catalytic reaction to give the corresponding propargylic amines with a high enantioselectivity. The results of some stoichiometric and catalytic reactions indicate that the catalytic amination proceeds via copper-allenylidene complexes formed in situ, where the attack of amines to the electrophilic gamma-carbon atom in the allenylidene complex is an important step for the stereoselection. Investigation of the relative rate constants for the reaction of several para-substituted propargylic acetates with N-methylanilines reveals that the formation of the copper-allenylidene complexes is involved in the rate-determining step. The result of the density functional theory calculation on a model reaction also supports the proposed reaction pathway involving copper-allenylidene complexes as key intermediates. The catalytic procedure presented here provides a versatile and direct method for the preparation of a variety of chiral propargylic amines." @default.
- W2026421941 created "2016-06-24" @default.
- W2026421941 creator A5017998169 @default.
- W2026421941 creator A5026858345 @default.
- W2026421941 creator A5029786629 @default.
- W2026421941 creator A5042344549 @default.
- W2026421941 creator A5078165812 @default.
- W2026421941 creator A5090867811 @default.
- W2026421941 date "2010-07-09" @default.
- W2026421941 modified "2023-09-30" @default.
- W2026421941 title "Copper-Catalyzed Enantioselective Propargylic Amination of Propargylic Esters with Amines: Copper−Allenylidene Complexes as Key Intermediates" @default.
- W2026421941 cites W1963812262 @default.
- W2026421941 cites W1964484777 @default.
- W2026421941 cites W1966792574 @default.
- W2026421941 cites W1967782701 @default.
- W2026421941 cites W1970567990 @default.
- W2026421941 cites W1970985296 @default.
- W2026421941 cites W1972456842 @default.
- W2026421941 cites W1974992646 @default.
- W2026421941 cites W1978502143 @default.
- W2026421941 cites W1979514772 @default.
- W2026421941 cites W1979982013 @default.
- W2026421941 cites W1986001811 @default.
- W2026421941 cites W1986789271 @default.
- W2026421941 cites W1988066093 @default.
- W2026421941 cites W1990367235 @default.
- W2026421941 cites W1990928456 @default.
- W2026421941 cites W1994136921 @default.
- W2026421941 cites W1997890645 @default.
- W2026421941 cites W1998761932 @default.
- W2026421941 cites W2000329614 @default.
- W2026421941 cites W2000872531 @default.
- W2026421941 cites W2003806837 @default.
- W2026421941 cites W2004787393 @default.
- W2026421941 cites W2005524060 @default.
- W2026421941 cites W2008336000 @default.
- W2026421941 cites W2008684086 @default.
- W2026421941 cites W2010789068 @default.
- W2026421941 cites W2012671593 @default.
- W2026421941 cites W2018914369 @default.
- W2026421941 cites W2019123141 @default.
- W2026421941 cites W2023271753 @default.
- W2026421941 cites W2023557482 @default.
- W2026421941 cites W2025667117 @default.
- W2026421941 cites W2027776332 @default.
- W2026421941 cites W2028389987 @default.
- W2026421941 cites W2028902552 @default.
- W2026421941 cites W2028960696 @default.
- W2026421941 cites W2031192939 @default.
- W2026421941 cites W2032404175 @default.
- W2026421941 cites W2033288172 @default.
- W2026421941 cites W2033427870 @default.
- W2026421941 cites W2038246555 @default.
- W2026421941 cites W2039515729 @default.
- W2026421941 cites W2046295809 @default.
- W2026421941 cites W2046337796 @default.
- W2026421941 cites W2048631643 @default.
- W2026421941 cites W2049095005 @default.
- W2026421941 cites W2051273129 @default.
- W2026421941 cites W2053836759 @default.
- W2026421941 cites W2056513115 @default.
- W2026421941 cites W2058916692 @default.
- W2026421941 cites W2059157945 @default.
- W2026421941 cites W2061555962 @default.
- W2026421941 cites W2062799381 @default.
- W2026421941 cites W2064558187 @default.
- W2026421941 cites W2066090507 @default.
- W2026421941 cites W2069815550 @default.
- W2026421941 cites W2074104510 @default.
- W2026421941 cites W2074588864 @default.
- W2026421941 cites W2079229933 @default.
- W2026421941 cites W2083572690 @default.
- W2026421941 cites W2083881560 @default.
- W2026421941 cites W2084223211 @default.
- W2026421941 cites W2085994150 @default.
- W2026421941 cites W2087919688 @default.
- W2026421941 cites W2089954501 @default.
- W2026421941 cites W2091609794 @default.
- W2026421941 cites W2092356369 @default.
- W2026421941 cites W2093552525 @default.
- W2026421941 cites W2094186244 @default.
- W2026421941 cites W2095077794 @default.
- W2026421941 cites W2095133124 @default.
- W2026421941 cites W2095777777 @default.
- W2026421941 cites W2096212408 @default.
- W2026421941 cites W2103380929 @default.
- W2026421941 cites W2107226133 @default.
- W2026421941 cites W2113380710 @default.
- W2026421941 cites W2121313057 @default.
- W2026421941 cites W2122127953 @default.
- W2026421941 cites W2122509398 @default.
- W2026421941 cites W2122938119 @default.
- W2026421941 cites W2123416667 @default.
- W2026421941 cites W2123536607 @default.
- W2026421941 cites W2125082952 @default.
- W2026421941 cites W2125250513 @default.
- W2026421941 cites W2128195098 @default.
- W2026421941 cites W2131397737 @default.