| Autor: |
Peng PK; Department of Chemistry, University of Houston, 3585 Cullen Blvd., Fleming Building 112, Houston, Texas 77204-5003, United States., May JA; Department of Chemistry, University of Houston, 3585 Cullen Blvd., Fleming Building 112, Houston, Texas 77204-5003, United States. |
| Jazyk: |
angličtina |
| Zdroj: |
Organic letters [Org Lett] 2022 Jul 29; Vol. 24 (29), pp. 5334-5338. Date of Electronic Publication: 2022 Jul 15. |
| DOI: |
10.1021/acs.orglett.2c01976 |
| Abstrakt: |
A bisperfluorotoluyl-BINOL catalyzed conjugate addition of trifluoroborate salts to doubly vinylogous esters and aldol condensation synthesized chiral δ-substituted cyclohexenones with high yields and enantioselectivities (10 examples, up to 89% yield, 89-98% ee). Stepwise and single-pot sequences were developed, with the former also providing β-substituted masked ketoaldehydes containing a vinyl ether. The transformation was used in a four-step total synthesis of penienone (24% overall yield), ≤ half the steps as in previous syntheses. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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