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. 2010 Apr 12;49(17):3069-72.
doi: 10.1002/anie.201000033.

Structurally and stereochemically diverse tetrahydropyran synthesis through oxidative C-H bond activation

Lei Liu  1 , Paul E Floreancig
Affiliations

Structurally and stereochemically diverse tetrahydropyran synthesis through oxidative C-H bond activation

Lei Liu et al. Angew Chem Int Ed Engl. .
No abstract available

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Figures

Scheme 1
Scheme 1
Vinylsilane classes.
Scheme 2
Scheme 2
Conformational control through 1,3-allylic strain minimization.
Scheme 3
Scheme 3
Vinylsilane products in cross-coupling reactions. dba =1,5-diphenyl-1,4-pentadien-3-one.
Scheme 4
Scheme 4
Cyclization reactions of propargylic ethers. DCE =dichloroethane.
Scheme 5
Scheme 5
Synthesis of a stereochemically diverse library. a) NaBH4, MeOH, −10°C, 85%. b) L-Selectride, THF, −90°C, 65% from 23, 89%from 24. c) PhMe2SiH, [Cp*Ru(NCCH3)3]PF6, acetone, 0 °C, 91% for 25, 92% for 28, 100% for 33, 86% from 35. d) PhMe2SiH, H2PtCl6·6H2O, THF, 50 °C, 65% for 26, 67% for 28, 64% for 34, 62%for 36. e) TBSCl, imidazole, CH2Cl2 or DMF. f) H2, Crabtree’s catalyst, CH2Cl2. g) CH3CO3H, KBr, NaOAc, HOAc, 53% from 25, 67% from 26.h) Bu4NF, THF, 50% from 27, 63% from 28, 67% from 33, 57% from34, 53% from 35, 58% from 36. i) SmI2, THF, iPrOH, 85%. Cp* = pentamethylcyclopentadienyl, Crabtree’s catalyst =[(cod)(py)(Cy3P)I]PF6–, L-Selectride =lithium tri(sec-butyl)borohydride, DMF =N,N-dimethylformamide, TBS=tert-butyldimethylsilyl. THF =tetrahydrofuran.
Scheme 6
Scheme 6
Stereoselective reduction of 2,6-trans isomers.
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