A Rh(III)-Catalyzed Formal [4+1] Approach to Pyrrolidines from Unactivated Terminal Alkenes and Nitrene Sources
We have developed a formal [4+1] approach to pyrrolidines from readily available unactivated terminal alkenes as 4-carbon partners. The reaction provides a rapid construction of various pyrrolidine containing structures, especially for the diastereoselect
Lee, Sumin,Lei, Honghui,Rovis, Tomislav
supporting information
p. 12536 - 12540
(2019/08/26)
Directing abilities of alcohol-derived functional groups in the hydroformylation of olefins
The hydroformylation of allylic and homoallylic alcohols and their derivatives using cationic and neutral rhodium complexes has been examined. The highest diastereoselectivity (87:13) was observed in the reaction of 1-methoxymethoxy-2-methylenecyclohexane. Higher yields and similar selectivities were obtained in the reaction of the TBDMS-protected alcohol. The major diastereomer results from hydroformylation syn to the functional group, which would suggest a directing effect. However, hydroformylation of 3-methylene-1-cyclohexanol derivatives occurs on the face opposite to the directing group in the major isomer. These data, in addition to the results of hydroformylation of 1-methyl-2-methylenecyclohexane, suggest that inherent conformational preferences are of significant importance in determining the product distribution and that the directing power of simple alcohols and their derivatives is moderate at best under the conditions examined in this study.
Ren, Li,Crudden, Cathleen M.
p. 1746 - 1750
(2007/10/03)
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