期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 4, 页码 2131-2144出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b03033
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资金
- DST, New Delhi, India
- IIT Kanpur, India
- CSIR, New Delhi, India
Two novel synthetic protocols for the syntheses of highly functionalized five-membered carbocyclic enaminonitriles and beta-enaminoesters have been developed via domino ring-opening cyclization (DROC) and DROC/decarboxylative tautomerization of activated cyclopropanes with malononitrile pronucleophiles, respectively. Both of the efficient strategies (yield up to 93%) have been generalized with various donor-acceptor and acceptor cyclopropanes as well as with malononitrile derivatives. The stereospecific variants of the two S(N)2-type DROC strategies have also been developed by employing enantiopure donor-acceptor (DA) cyclopropanes to synthesize the corresponding nonracemic products with excellent stereoselectivities (dr up to >99:1, ee up to >99%).
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