Journal
TETRAHEDRON
Volume 75, Issue 16, Pages 2436-2445Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2019.03.012
Keywords
Oxonium ylide; Rearrangement; Rhodium; Chemoselectivity; Stereoselectivity
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Funding
- Japan Society for the Promotion of Science (JSPS) [JP16K08158]
- JSPS Core-to-Core Program, B. Asia-Africa Science Platforms
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Dirhodium(II)-catalyzed oxonium ylide formation-[2,3]-sigmatropic rearrangement of 6-allyloxy-2-diazo-3-ketoesters possessing a C-6 substituent is described. The reaction of 6-alkyl- or 6-aryl-substituted 6-allyloxy-2-diazo-3-ketoesters with a catalytic amount of Rh-2(S-PTTL)(4) proceeded in a chemoselective and stereoselective manner to provide 6-substituted 2-allyl-3-oxotetrahydropyran-2-carboxylates in good yields and with high diastereoselectivities. To demonstrate the utility of this sequential reaction, we conducted the total synthesis of (+)-tanikolide, in which the construction of the delta-lactone skeleton was achieved by employing a 2-iodobenzamide-catalyzed oxidative cleavage of tetrahydropyran-2-methanol. (C) 2019 Elsevier Ltd. All rights reserved.
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