Abstract
Original language | English |
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Pages (from-to) | 10392–10400 |
Number of pages | 9 |
Journal | ACS Catalysis |
Volume | 8 |
Issue number | 11 |
DOIs | |
Publication status | Published - 27 Sep 2018 |
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Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of Enoldiazocarbonyl Compounds. / Marichev, Kostiantyn; Adly, Frady G.; Carranco, Alejandra; Garcia, Estevan; Arman, Hadi; Doyle, Michael.
In: ACS Catalysis, Vol. 8, No. 11, 27.09.2018, p. 10392–10400.Research output: Contribution to journal › Article
TY - JOUR
T1 - Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of Enoldiazocarbonyl Compounds
AU - Marichev, Kostiantyn
AU - Adly, Frady G.
AU - Carranco, Alejandra
AU - Garcia, Estevan
AU - Arman, Hadi
AU - Doyle, Michael
PY - 2018/9/27
Y1 - 2018/9/27
N2 - Chiral copper(I) catalysts are preferred over chiral dirhodium(II) catalysts for [3 + 3]-cycloaddition reactions of enoldiazocarbonyl compounds with nitrones and acyliminopyridinium ylides, forming chiral oxazines and pyrazines in very high yield and enantioselectivity. Yields and stereoselectivities from reactions of enoldiazoketones are virtually the same as those from the corresponding esters and amides, but products from enoldiazoketones are precursors to chiral 1,3-dicarbonyl derivatives that provide additional opportunities in heterocyclic synthesis through the formation of pyrazoles and isoxazoles.
AB - Chiral copper(I) catalysts are preferred over chiral dirhodium(II) catalysts for [3 + 3]-cycloaddition reactions of enoldiazocarbonyl compounds with nitrones and acyliminopyridinium ylides, forming chiral oxazines and pyrazines in very high yield and enantioselectivity. Yields and stereoselectivities from reactions of enoldiazoketones are virtually the same as those from the corresponding esters and amides, but products from enoldiazoketones are precursors to chiral 1,3-dicarbonyl derivatives that provide additional opportunities in heterocyclic synthesis through the formation of pyrazoles and isoxazoles.
KW - Chrial catalysts
KW - bisoxazoline ligands
KW - copper
KW - cycloaddition
KW - heterocycles
KW - metal carbene
U2 - 10.1021/acscatal.8b03391
DO - 10.1021/acscatal.8b03391
M3 - Article
VL - 8
SP - 10392
EP - 10400
JO - ACS Catalysis
JF - ACS Catalysis
SN - 2155-5435
IS - 11
ER -