Prins–Arylthiolation Reaction on Terpenoids: Diastereoselective Synthesis of 4‐Arylthiooctahydro‐2 H ‐chromenes | Zendy

Sarmah Barnali | Zendy; Baishya Gakul | Zendy; Baruah Rajani K. | Zendy

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Prins–Arylthiolation Reaction on Terpenoids: Diastereoselective Synthesis of 4‐Arylthiooctahydro‐2 H ‐chromenes

Author(s) -

Sarmah Barnali,

Baishya Gakul,

Baruah Rajani K.

Publication year - 2014

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.201403080

Subject(s) - prins reaction , chemistry , dichloromethane , cyclohexanone , selectivity , terpenoid , domino , catalysis , organic chemistry , hemiacetal , stereochemistry , solvent

(–)‐Isopulegol undergoes Prins‐arylthiolation with different aldehydes and cyclohexanone in the presence of HBF 4 · OEt 2 to generate a library of 4‐arylthiooctahydro‐2 H ‐chromene derivatives in good to excellent yields with moderate to high cis selectivity at ambient temperature in dichloromethane. Readily available HBF 4 · OEt 2 as a catalyst outshines CF 3 CO 2 H, which is generally used in excess amounts in Prins cyclization and domino Prins‐arylthiolation reactions.

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