Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 16, Pages 8984-8994Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b01170
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Funding
- National Natural Science Foundation of China [21202152]
- Natural Science Foundation of Zhejiang Province [LY16B020003]
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The selective construction of bicyclo[3.3.0]octan-1-ols and bicyclo[3.1.0]hexan-1-ols was achieved by using an allylSmBr/additive(s) system. By employing HMPA as the only additive, the momoallylation/ketone-alkene coupling occurred preferably and afforded bicyclo[3.3.0]octan-1-ols in good yields with high diastereoselectivities. While the ester-alkene coupling predominated to generate bicyclo[3.1.0]hexan-1-ols in moderate yields with excellent diastereoselectivities in the presence of a proton source, such as pyrrole as the coadditive with HMPA. The tunable reactivity of allylSmBr by additive(s) would make it a versatile reagent in organic synthesis.
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