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Stereospecific, Flexible and Redox‐Economic Asymmetric Synthesis of cis ‐ and trans ‐3‐Hydroxypipecolic Acids and Analogs
Author(s) -
Wang Bing,
Liu RunHua
Publication year - 2009
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.200900231
Subject(s) - chemistry , stereospecificity , oxazoline , stereochemistry , pipecolic acid , enantioselective synthesis , redox , cleavage (geology) , combinatorial chemistry , ring (chemistry) , organic chemistry , catalysis , amino acid , biochemistry , geotechnical engineering , fracture (geology) , engineering
Abstract Both cis ‐ and trans ‐3‐hydroxy‐ L ‐pipecolic acids are synthesized from a common chiral intermediate 7 by a short and flexible route. The stereospecific inversion of C‐3 was achieved by the formation of an oxazoline followed by acidic ring cleavage. The overall yields are 27 % and 30 %, respectively, in 12 and 10 linear steps. Several versatile chiral building blocks are also accessible by this diastereodivergent synthesis. Unlike the chiral pool approach, our synthetic strategy is not limited by the availability of starting materials.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)