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N,Se‐Acetals: Preparation and use in diastereoselective radical reactions
Author(s) -
Stojanovic Aleksandar,
Renaud Philippe
Publication year - 1998
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19980810216
Subject(s) - chemistry , steric effects , stereoselectivity , radical cyclization , medicinal chemistry , stereochemistry , organic chemistry , computational chemistry , catalysis
A new facile synthesis of N,S‐ and N,Se‐acetals starting from aldehydes and primary amines is presented ( Schemes 3–5 ). These acetals are used as precursors for stereoselective radical deuteration and allylation reactions ( Schemes 6 and 7, Tables 1 and 2 ). The stereochemical outcome of the reactions depends on the radical trap and the substituents at the N‐atom. Deuterations give always anti products with moderate to high selectivities. The allylation reactions give either syn or anti products with low to moderate selectivities. The observed stereoselectivities can be explained with a model based on minimization of A 1,3 strain and are controlled by steric and stereoelectronic effects.