Dramatic influence of ester steric hindrance on the diastereoselectivity of a Michael addition towards the synthesis of the ABC tricycle of hexacyclinic acid

Autor:	Raphaël Oriez, Alexandre Audic, Joëlle Prunet
Jazyk:	angličtina
Rok vydání:	2021
Předmět:	Steric effects 010405 organic chemistry Chemistry Stereochemistry Organic Chemistry Diastereomer Hexacyclinic acid 010402 general chemistry Ring (chemistry) 01 natural sciences Biochemistry 0104 chemical sciences Drug Discovery Michael reaction Conjugate
ISSN:	0040-4020
Popis:	During our studies toward the synthesis of the ABC ring system of hexacyclinic acid, we observed an unexpected influence of the steric bulk of the ester group of the Michael acceptor in a key conjugate addition. We propose an eight-membered ring transition state to explain the formation of the undesired diastereomer in the case of unhindered esters.
Databáze:	OpenAIRE
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