By Gabriel Tojo
This e-book is a needs to for somebody all in favour of the training of natural compounds. it's the first one in a brand new sequence on easy reactions in natural synthesis. It offers lots of particular and valuable details within the useful elements of the oxidation of alcohols to aldehydes and ketones, that's the most very important response within the synthesis of natural compounds.
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Additional info for Oxidation of Alcohols to Aldehydes and Ketones: A Guide to Current Common Practice
5 h, giving a 70% yield. In the absence of both molecular sieves and acetic acid, the reaction takes 3 d at 408C and provides a 70% yield. 7 eq. PDC, 3 eq. Ac2O CH2Cl2, 3 h, 40 ЊC O TBSO OTMSEt OTBS 84% Ref. 135 The addition of Ac2 O allows a smooth high-yielding reaction. HO O 1 eq. 5 eq. t. HO OH HO O HO O 52% Ref. 127b Molecular sieves are not added because they promote a quick, non-selective oxidation. The addition of acetic acid is needed for a smooth and complete oxidation. 2. Functional Group and Protecting Group Sensitivity to Oxidation with PDC The near neutral character of PDC makes almost all protecting groups, including very acid sensitive ones, resistant to its action.
T. OMe OMe O O 71% Ref. 147 This reaction succeeds with PDC, with no interference from the hindered secondary amine, while Dess-Martin periodinane and tetra-n-propylammonium perruthenate give complex mixtures. 148 Although N-methyl tertiary amines are transformed into formamides by PDC,149 this reaction is usually slow enough so that selective oxidation of alcohols with PDC can be possible. 150 N-Methyl aromatic amines can suVer oxidation by PDC, giving an immonium ion that can be trapped intramolecularly by a neighbouring alcohol.
Greig, N. ; Holloway, H. ; Whittaker, N. -sheng; Tetrahedron Lett. 2000, 41, 4861. Lett. 1990, 1, 109. 151 Yli-Kauhaluoma, J. ; Harwig, C. ; Janda, K. ; Tetrahedron Lett. 1998, 39, 2269. ; Sundaram, S. Soc. 1991, 68, 77. Acta 2002, 85, 1989. Chem. 1999, 64, 394. Commun. 2000, 18, 1783. Bull. 1989, 37, 1691. c) Parker, K. Chem. 1987, 52, 4369. ; Tetrahedron Lett. 1997, 38, 1589. Lett. 1993, 3, 1859. c) Kozikowski, A. ; Fauq, A. ; Synlett 1991, 11, 783. ; Rawson, D. ; Tetrahedron Lett. 1989, 30, 7463.