References
- Shiao , M.-J. , Yang , C.-Y. , Lee , S.-H. and Wu , T.-C. 1988 . Synth. Commun. , 18 : 359 The reported procedure was adapted to provide large quantity of the silyloxyacetaldehyde 3 without chromatography. To a cold (-78 °C) solution of tert-butyldiphenylsilyl chloride (89.2 g, 325 mmol) and DMAP (3.97 g, 32.5 mmol) in THF (530 mL) stirred with a mechanical stirrer, a solution of solketal (40.3 mL, 324 mmol) and triethylamine (50 mL, 359 mmol) in THF (30 mL) was added dropwise over a period of 40 min. The reaction was allowed to warm to room temp and stirred overnight. The white slurry was filtered and the white solid washed with hexane (five times). The combined filtrate was concentrated, and the residue triturated with hexane, and was then filtered. The filtrate was concentrated in vacuo to provide 124 g of the crude silyl ether as clear colorless viscous oil. Without further purification, a solution of the above silyl ether (26.7 g, 72 mmol) and aq. HCl (72 mL, 2 M) in THF (360 mL) was stirred at room temp overnight. The resultant mixture was concentrated in vacuo to remove most of the THF. The residue was diluted with ethyl acetate, and washed successively with sat. NaHCO3 and brine. The organic extract was dried (MgSO4), filtered, concentrated in vacuo, triturated with hexane, and cooled to 0 °C. The white solid was filtered, washed with ice-cold hexanes, stored in vacuo overnight, to provide 22 g (93%) of analytical pure 1-tert-butyldiphenylsilyloxy-2,3-propanediol. Oxidation to the aldehyde 3 was carried out as reported
- Whitesides , G. M. , Casey , C. P. and Krieger , J. K. 1971 . J. Am. Chem. Soc. , 93 : 1379
- Gao , Y. , Hanson , R. M. , Klunder , J. M. , Ko , S. Y. , Masamune , H. and Sharpless , K. B. 1987 . J. Am. Chem. Soc. , 109 : 5765 Attempts to run the kinetic resolution under catalytic conditions were not successful
- Susuki , T. , Sato , E. and Unno , K. 1986 . J. Chem. Soc. Perkin Trans. I , : 2263
- Hanessian , S. and Lavallee , P. 1975 . Can. J. Chem. , 53 : 2975
- Corey , E. J. , Kim , C. U. and Takeda , M. 1972 . Tetrahedron Lett. , 13 : 4339
- Reaction of an optically pure lactam with bromide 1a led to a single diastereomer. The 1H NMR spectrum of which showed only a set of signals for the allylic protons (CH=CHCH2N), versus the two sets observed with products derived from alkylation with racemic 1a.8 This indicated that the enantiomerically enriched 1a was >s96% optically pure
- Racemic 1a was prepared in a similar manner with omission of the kinetic resolution step. Furthermore, a much cheaper mixture of trans and cis 1-bromo-1-propene could be used instead of the more costly pure trans 1-bromo-1-propene. After the Claisen rearrangement, no spectroscopic difference was observed between products derived from pure trans propene versus those from the trans/cis mixture
- Jung , M. E. and Light , L. A. 1982 . Tetrahedron Lett. , 23 : 3851
- Chen , S.-M. L. , Schaub , R. E. and Grudzinskas , C. V. 1978 . J. Org. Chem. , 43 : 3450
- Kasatkin , A. N. , Biktimirov Kh , R. , Kulak , A. N. and Tolstikov , G. A. 1991 . Zh. Org. Khim. , 27 : 712
- Munch-Petersen , J. , Bretting , C. , Jorgensen , P. M. , Refn , S. and Andersen , V. K. 1961 . Acta Chem. Scand. , 15 : 277 Following Munch-Petersen et al. reported protocol, treatment of either isopropyl or tert-butyl 6-tert-butyldiphenylsilyloxy-E,E-2,3–4,5-hexadienoate with 2-fluorobenzyl magnesium chloride provided predominately the 1,2 instead of the 1,4 addition product. Cf
- Evans , D. A. , Kaldor , S. W. , Jones , T. K. , Clardy , J. and Stout , T. J. 1990 . J. Am. Chem. Soc. , 112 : 7001
- Nahm , S. and Weinreb , S. M. 1981 . Tetrahedron Lett. , 22 : 3815
- Kasatkin , A. N. , Biktimirov , Kh. R. , Tolstikov , G. A. and Khalilov , L. M. 1990 . Zh. Org. Khim. , 26 : 1191
- Kim , S. and Park , J. H. 1988 . J. Org. Chem. , 53 : 3111