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Regioselective Deuteration of a 3,4‐Dialkoxypyrroline N ‐Oxide and Synthesis of 8a‐ d ‐Indolizidines
Author(s) -
Ranzenigo Anna,
Mercurio Chiara,
Karrenbrock Maurice,
Cordero Franca M.,
Cardini Gianni,
Pagliai Marco,
Brandi Alberto
Publication year - 2020
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.202000402
Subject(s) - chemistry , nitrone , regioselectivity , deuterium , combinatorial chemistry , oxide , hydrogen–deuterium exchange , base (topology) , stereochemistry , computational chemistry , organic chemistry , catalysis , hydrogen , cycloaddition , mathematical analysis , physics , mathematics , quantum mechanics
A simple and efficient method for C‐2 deuterium labeling of 3,4‐di‐ tert ‐butoxypyrroline N ‐oxide, a useful chiral building block in azaheterocycles syntheses, is presented. Selective and quantitative deuterium incorporation (> 99 %) was achieved by base‐catalyzed H/D exchange in D 2 O under mild reaction conditions. A mechanistic pathway based on kinetic and computational data was proposed. The labeled nitrone was used in the synthesis of C‐8a deuterated (1 R ,2 R ,8a R )‐lentiginosine.