Selectivity in Cationic Cyclizations Involving Alkynes: A Computational Study on the Biomimetic Synthesis of Steroids

• Published in: Chemistry : a European journal Vol. 29; no. 19; pp. e202204028 - n/a
• Main Authors: Cózar, Abel, Arrieta, Ana, Cossío, Fernando P.
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 03.04.2023
• Subjects: Alkynes; Biomimetics; Chemistry; computational chemistry; Computer applications; cyclization reactions; distortion/Interaction activation strain model; Epoxides; reaction mechanisms; Stereochemistry; Steroid hormones; Steroids; reaction mechanisms; cyclization reactions; distortion/Interaction activation strain model; computational chemistry

Computational studies on the electrophilic cyclization between alkynes and transient carbocations or Lewis‐acid‐activated epoxides show that the regiochemistry of the reaction depends on the terminal or internal position of the triple bond. Reactants possessing terminal alkynyl groups lead to six‐me...