Diastereoselective reductive aldol reactions of Boc-protected electron deficient pyrroles |
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| Authors: | Timothy J. Donohoe David House |
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| Affiliation: | Dyson Perrins Laboratory, South Parks Road, Oxford OX1 3QY, UK |
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| Abstract: | An anti-selective reductive aldol reaction of a Boc-protected, 2-substituted pyrrole is reported. Reduction with LiDBB generates an exocyclic lithium enolate, but optimal stereoselectivity is obtained by transmetallation to magnesium with MgBr2·OEt2. The corresponding syn-aldols can easily be obtained (protected as carbamates) by subsequent inversion. |
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| Keywords: | aldol reaction chelation Lewis acids LiDBB partial reduction |
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