Cyclopropane Structural Units from Homoaldol Adducts

Cyclopropane Structural Units from Homoaldol Adducts

An efficient two-step homologation of aldehydes to cyclopropylaldehydes has been developed. Activation of homoaldol adducts derived from O-enecarbamates and N-enecarbamates provided high yields of cyclopropylaldehydes with good to excellent levels of trans/cis selectivity. Trapping of the intermedia...

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Veröffentlicht in:Organic letters 2003-04, Vol.5 (8), p.1377-1379
Hauptverfasser: Taylor, Richard E, Risatti, Christina A, Engelhardt, F. Conrad, Schmitt, Michael J
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container_title Organic letters
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creator Taylor, Richard E
Risatti, Christina A
Engelhardt, F. Conrad
Schmitt, Michael J
description An efficient two-step homologation of aldehydes to cyclopropylaldehydes has been developed. Activation of homoaldol adducts derived from O-enecarbamates and N-enecarbamates provided high yields of cyclopropylaldehydes with good to excellent levels of trans/cis selectivity. Trapping of the intermediate oxonium ion and iminium ion intermediates has also been demonstrated, leading to direct isolation of cyclopropyl carbinol and cyclopropylamine products.
doi_str_mv 10.1021/ol034448r
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title Cyclopropane Structural Units from Homoaldol Adducts
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