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Highly Diastereoselective Reaction of α‐Diazoesters with Aryl Alcohols and Isatin Imines: Rapid Access to Oxindole‐Derived α‐Alkoxy‐β‐amino Acid Derivatives with Two Adjacent Quaternary Carbon Centers
Author(s) -
Rajasekaran Tamilselvan,
Karthik Govindaraju,
Sridhar B.,
Kumar S. Kiran,
Reddy Basi V. Subba
Publication year - 2014
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.201301775
Subject(s) - chemistry , isatin , oxindole , alkoxy group , yield (engineering) , malononitrile , aryl , indoline , stereoselectivity , enantioselective synthesis , catalysis , quaternary carbon , organic chemistry , medicinal chemistry , stereochemistry , alkyl , materials science , metallurgy
A stereoselective synthesis of oxindole‐derived α‐alkoxy‐β‐amino acid derivatives was achieved in high yield with excellent diastereoselectivity through the three‐component reaction of methyl 2‐diazoarylacetate, aryl alcohols, and isatin‐derived ketimines by using Rh 2 (OAc) 4 (1 mol‐%) as the catalyst. The products are very useful for the synthesis of analogues of the gastrin receptor antagonist AG‐041R, spirooxindolyl β‐lactams, the oxindole‐derived side chain of Taxol, and natural product cytoxazone and aminopyrrolo[2,3‐ b ]indoline derivatives.