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Regiospezifische Reduktionen von 1,3,3‐trisubstituierten Succinimiden mit Diboran
Author(s) -
Süess Rudolf
Publication year - 1977
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.19770600520
Subject(s) - chemistry , succinimides , diborane , yield (engineering) , steric effects , stereochemistry , medicinal chemistry , organic chemistry , boron , materials science , metallurgy
Regiospecific reduction of 1,3,3‐trisubstituted succinimides by diborane It is possible to reduce 1,3,3‐trisubstituted succinimides regiospecifically by diborane at the less substituted carbonyl group to yield the corresponding lactams. This method was used specially for the reduction of 2,8‐diazaspiro[4,5]decane‐1,3‐diones to 2,8‐diazaspiro[4,5]decan‐1‐ones. These results are in contrast to those of Speckamp et al. [4a‐h] in which sodiumborohydride/HCl was the reducing agent. Possible explanations for the selective reductions are discussed, using the principles of steric approach control of Dunitz & Bürgi [6] and of Baldwin [8].