α-Alkoxyorganolithium Reagents. A New Class of Configurationally Stable Carbanions for Organic Synthesis

Journal of the American Chemical Society

Volumn 102, Issue 3, 1980, Pages 1201-1202

  Still, W Clark ^a   Sreekumar, C ^a  

^a Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000588779     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00523a066     Document Type: Article

References (11)

1. B. L. Letsinger, Angew. Chem., 70, 151 (1958), and references cited therein; E. Grovenstein, Jr., and Y.-M. Cheng, Chem. Commun., 101 (1970); M. J. S. Dewar and J. M. Harris, J. Am. Chem. Soc., 91, 3652 (1969).
2. D. Y. Curtin and W. J. Koehl, J. Am. Chem. Soc., 84, 1967 (1962).
3. W. C. Still, J. Am. Chem. Soc., 100, 1481 (1978).
4. J. A. Dale, D. L. Dull, and H. S. Mosher, J. Org. Chem., 34, 2543 (1969); S. L. Chen, K. Nakanishi, M. Morisaki, N. Ikehawa, and Y. Shimizu, J. Am. Chem. Soc., 97, 5297 (1975), and references cited therein.
5. Optical resolution of the tributyltin adduct of propanal could also be effected via formation of a urethane with (-)-a;-phenylethylamine [(a) COCl2, l-Pr2NEt
6. Although no peaks resulting from the (’)-MTPA ester of the enantiomeric alcohol could be seen, proportions of that material as large as 5% could have escaped detection.
7. D. J. Cram and F. A. Abd Elhafez, J. Am. Chem. Soc., 74, 5828, 5851 (1952). See also N. T. Ahn and 0. Eisenstein, Nouv. J. Chim., 1, 61 (1977).
8. D. J. Cram and K. R. Kopecky, J. Am. Chem. Soc., 81, 2748 (1959); D. J. Cram and D. R. Wilson, J. Am. Chem. Soc., 85, 1245 (1963).
9. Assuming retention of stereochemistry during methylatlon.
10. Authentic threo material was prepared from tiglic acid as follows: (1) LiAIH4, EtsO; (2) BnOCHsCI, i-PrsNEt; (3) BH3, THF; NaOH, H2O2; (4) MeOCHsCI, i-PraNEt.
11. Alfred P. Sloan Fellow, 1978-1980.