Journal
ACS CATALYSIS
Volume 7, Issue 6, Pages 3763-3767Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b00590
Keywords
alkynones; alpha-angelica lactone; gamma-alkenyl butenolides; N,N'-dioxides; scandium
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Funding
- National Natural Science Foundation of China [21290182]
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The asymmetric synthesis of gamma-alkenyl butenolides was accomplished by conjugated addition of butenolides to alkynones. Both terminal alkynones and nonterminal alkynones were applicable to the N,N'-dioxide scandium(111) catalytic system. The corresponding products were obtained in good to excellent yields (up to 99%) with high E/Z ratios and high enantioselectivities (up to 98% ee). The novel methods of building both y-alkenyl butenolides and continuing epoxidation products facilitated constructing core structure of biologically active natural products and synthetic intermediates. Additionally, one-pot Michael addition/epoxidation performed well with our catalytic system.
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