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Asymmetric Synthesis of Substituted Prolines by 1,3‐Dipolar Cycloadditions of Azomethine Ylides from Chiral 6‐Isopropyl‐5‐phenylmorpholin‐2‐ones
Author(s) -
Chinchilla Rafael,
Falvello Larry R.,
Galindo Nuria,
Nájera Carmen
Publication year - 2001
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 - 10.1002/1099-0690(200108)2001:16<3133::aid-ejoc3133>3.0.co;2-o
Subject(s) - chemistry , isopropyl , cycloaddition , glycine , selectivity , azomethine ylide , 1,3 dipolar cycloaddition , stereochemistry , alanine , amino acid , organic chemistry , catalysis , biochemistry
Chiral saturated alanine‐ and glycine‐derived 6‐isopropyl‐5‐phenylmorpholin‐2‐ones 11 and 12 have been prepared and employed for the generation of carboxy‐stabilized ylides in asymmetric 1,3‐dipolar cycloaddition reactions under thermal conditions, with electron‐deficient dipolarophiles bearing double and triple bonds. The cycloadducts are obtained with high stereocontrol and mainly with endo selectivity, and can be used for the synthesis of highly substituted enantiomerically pure prolines.