cis-Dihydroxylated α-Trifluoromethylated N,O-Acetal from l-Tartaric Acid: Synthesis of Tetrasubstituted Stereocenter via Diastereoselective Pictet-Spengler Cyclization of N-Acyliminium Ions | Zendy

Abdelkhalek Ben Jamaa | Zendy; Mohammed Latrache | Zendy; Emmanuel Riguet | Zendy; Fabienne Grellepois | Zendy

Open Access

cis-Dihydroxylated α-Trifluoromethylated N,O-Acetal from l-Tartaric Acid: Synthesis of Tetrasubstituted Stereocenter via Diastereoselective Pictet-Spengler Cyclization of N-Acyliminium Ions

Author(s) -

Abdelkhalek Ben Jamaa,

Mohammed Latrache,

Emmanuel Riguet,

Fabienne Grellepois

Publication year - 2020

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.0c00801

Subject(s) - chemistry , stereocenter , moiety , enantiopure drug , acetal , tartaric acid , substituent , trifluoromethyl , electrophile , triflic acid , stereochemistry , oxonium ion , enantioselective synthesis , medicinal chemistry , organic chemistry , alkyl , ion , catalysis , citric acid

The synthesis of cyclic, chiral α-trifluoromethylated N , O -acetals having a protected cis -diol moiety has been readily achieved in two steps from a known bis-Weinreb amide derived from l-tartaric acid. The reaction of O -acetyl analogues of these N , O -acetals with triflic acid in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) at 0 °C generated in situ he corresponding electrophilic α-trifluoromethyl N -acyliminium ions that undergo Pictet-Spengler-type cyclizations. After only 10 min of reaction, the original enantiopure aza-tricyclic scaffolds bearing a trifluoromethyl substituent at the bridgehead position were obtained with diastereoselectivities ranging from 75:25 to 97:3.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research