References
- Corey , E. J. and Link , J. O . 1992 . J. Am. Chem. Soc. , 114 : 1906
- Mizawa , T. , Takashima , K. , Mitsuda , Y. , Yamada , T. , Kuwata , S. and Watanabe , H. 1979 . Bull. Chem. Soc. Jpn. , 52 : 1539
- Davies , H. M. L. and Cantrell , W. R. 1991 . Tetrahedron Lett. , 32 ( 45 ) : 6509
- Coppola , G. A. and Schuster , H. F. 1987 . Asymmetric Synthesis , 120 – 126 . J. Wiley . For a review of the use of L-tert leucine in asymmetric synthesis see: and references cited therein
- Evans , D. A. , Faul , M. M. , Bilodeau , M. T. , Anderson , B. A. and Barnes , D. M. 1993 . J. Amer. Chem. Soc. , 115 : 5328 For leading references see
- Meyers , A. I. and Shipman , M. 1991 . J. Org. Chem. , 56 : 7098
- Brandstrom , A. , Lamm , L. and Palmertz , I. 1974 . Acta Chem. Scand. , 28B : 699
- Dale , J. A. , Dull , D. L. and Mosher , H. S. 1969 . J. Org. Chem. , 34 : 2543
- Cooper , R. D. G. , Jose , F. , McShane , L. and Koppel , G. A. 1978 . Tetrahedron Lett. , 19 : 2243 For a similar transformation on homoserine lactone see
- Laginnis , E. D. and Chenard , B. L. 1984 . Tetrahedron Lett. , 25 : 5831
- Mancuso , A. J. , Huang , S. L. and Swern , D. 1978 . J. Org. Chem. , 43 : 2480
- Unpublished results of David Ripin
- We have never had any problems vacumn drying the reagent over P2O5 however, as with any azide, one should use caution. Excess azide has been used in solution with no loss in yield, and without concurrent isolation of intermediates 4 and 5, however chromatographic purification of 3a to remove (n-Bu)4N+ -OTf is necessary
- The main impurity is a 1:1 epimeric mixture of lactols which are easily separated from 8 by chromatography