Unknown

Dataset Information

0

Organometallic enantiomeric scaffolding. Sequential semipinacol/1,5-"Michael-like" reactions as a strategic approach to bridgehead-quaternary center aza[3.3.1]bicyclics: application to the total synthesis of (-)-adaline.


ABSTRACT: A nontraditional approach to the enantiocontrolled construction of quaternary center-bearing heteroatom-bridged bicyclo[3.3.1]nonanes (homotropanes) is reported that is based on organometallic enantiomeric scaffolding. This strategy takes advantage of the unique reactivity profiles of TpMo(CO)(2)(5-oxo-eta(3)-pyranyl) and TpMo(CO)(2)(5-oxo-eta(3)-pyridinyl) scaffolds, and features a molybdenum-mediated semipinacol/1,5-"Michael-like" reaction sequence to establish the quaternary center and synthesize the bridged bicyclic structure. An asymmetric total synthesis of (-)-adaline highlights this methodology.

SUBMITTER: Coombs TC 

PROVIDER: S-EPMC2654255 | biostudies-literature |

REPOSITORIES: biostudies-literature

Similar Datasets

| S-EPMC3648293 | biostudies-literature
| S-EPMC3107969 | biostudies-literature
| S-EPMC3790395 | biostudies-other
| S-EPMC2736330 | biostudies-literature
| S-EPMC2757657 | biostudies-literature
| S-EPMC3379287 | biostudies-literature
| S-EPMC7781395 | biostudies-literature
| S-EPMC3099911 | biostudies-literature
| S-EPMC9051536 | biostudies-literature
| S-EPMC2980113 | biostudies-literature