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- Title
Catalytic S<sub>N</sub>2′- and Enantioselective Allylic Substitution with a Diborylmethane Reagent and Application in Synthesis.
- Authors
Shi, Ying; Hoveyda, Amir H.
- Abstract
A catalytic method for the site- and enantioselective addition of commercially available di-B(pin)-methane to allylic phosphates is introduced (pin=pinacolato). Transformations may be facilitated by an NHC-Cu complex (NHC=N-heterocyclic carbene) and products obtained in 63-95 % yield, 88:12 to >98:2 SN2′/SN2 selectivity, and 85:15-99:1 enantiomeric ratio. The utility of the approach, entailing the involvement of different catalytic cross-coupling processes, is highlighted by its application to the formal synthesis of the cytotoxic natural product rhopaloic acid A.
- Subjects
CHEMICAL synthesis; PHOSPHATES; ENANTIOSELECTIVE catalysis; METHANE synthesis; CHEMICAL reagents; PHOSPHORUS compound synthesis
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 10, p3455
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201600309