Unknown

Dataset Information

0

Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles.

ABSTRACT: A highly efficient phosphine-catalyzed enantioselective [4 + 2] annulation of allenoates with 3-nitroindoles or 3-nitrobenzothiophenes has been developed. The protocol represents a unique dearomatization-aromatization process to access functionalized dihydrocarbazoles or dihydrodibenzothiophenes with high optical purity (up to 97% ee) under mild reaction conditions. The synthetic utility of the highly enantioselective [4 + 2] annulation enables a concise synthesis of analgesic agent.

SUBMITTER: Wang H 

PROVIDER: S-EPMC6995259 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Enantioselective [4+2] Annulation to the Concise Synthesis of Chiral Dihydrocarbazoles.

Wang Haiyang H   Hu Qingdong Q   Wang Mingxu M   Guo Chang C  

iScience 20200117 2

A highly efficient phosphine-catalyzed enantioselective [4 + 2] annulation of allenoates with 3-nitroindoles or 3-nitrobenzothiophenes has been developed. The protocol represents a unique dearomatization-aromatization process to access functionalized dihydrocarbazoles or dihydrodibenzothiophenes with high optical purity (up to 97% ee) under mild reaction conditions. The synthetic utility of the highly enantioselective [4 + 2] annulation enables a concise synthesis of analgesic agent. ...[more]

Similar Datasets

Unknown Enantioselective synthesis of planar chiral ferrocenes via palladium-catalyzed annulation with diarylethynes.
| S-EPMC3778326 | biostudies-literature
Unknown A concise enantioselective synthesis of (-)-ranirestat.
| S-EPMC2850125 | biostudies-literature
Unknown Concise, enantioselective total synthesis of (-)-alstonerine.
| S-EPMC2516964 | biostudies-literature
Unknown Concise synthesis of pauciflorol F using a Larock annulation.
| S-EPMC2787984 | biostudies-literature
Unknown A concise enantioselective synthesis of the chlorosulfolipid malhamensilipin A.
| S-EPMC2830791 | biostudies-literature
Unknown A concise enantioselective synthesis of the guaiane sesquiterpene (-)-oxyphyllol.
| S-EPMC3817518 | biostudies-literature
Unknown Highly enantioselective catalytic synthesis of chiral pyridines.
| S-EPMC5727103 | biostudies-other
Unknown A Concise, Enantioselective Approach for the Synthesis of Yohimbine Alkaloids.
| S-EPMC7185878 | biostudies-literature
Unknown N-Heterocyclic Carbene and Chiral Bronsted Acid Cooperative Catalysis for a Highly Enantioselective [4+2] Annulation.
| S-EPMC5496987 | biostudies-literature
Unknown Enantioselective, Convergent Synthesis of the Ineleganolide Core by a Tandem Annulation Cascade.
| S-EPMC5321630 | biostudies-literature