Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 72, Issue 14, Pages 5421-5423Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo0706271
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A samarium-promoted synthesis of (E)-nitroalkenes from 1-bromo-1-nitroalkan-2-ols in high yields and with total selectivity is reported. This reaction together with the easy and efficient preparation of the 1-bromo-1-nitroalkan-2-ols constitutes a simple and advantageous alternative toward nitroalkenes with total E-stereoselectivity. A mechanism is proposed to explain the E-stereoselectivity of the beta-elimination reaction.
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