Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2009, Issue 17, Pages 2845-2851Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200900231
Keywords
Asymmetric synthesis; Amino acids; Amino alcohols; Total synthesis
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Funding
- National Natural Science Foundation of China [20602008, 20832005]
- Fudan University [EYH1615003]
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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. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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