A Simple Stereoselective Version of the Claisen Rearrangement Leading to trans-Trisubstituted Olefinic Bonds. Synthesis of Squalene

Journal of the American Chemical Society

Volumn 92, Issue 3, 1970, Pages 741-743

  Johnson, William S ^a   Werthemann, Lucius ^a   Bartlett, William R ^a   Brocksom, Timothy J ^a   Li, Tsung Tee ^a   Faulkner, D John ^b   Petersen, Michael R ^b  

^a STANFORD UNIVERSITY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001685085     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00706a074     Document Type: Article

References (10)

1. We have found also that an analogous stereospecific reaction occurs on heating 1-dimethylamino-1,1-dimethoxyethane [A. E. Wick, D. Felix, K. Steen, and A. Eschenmoser, Helv. Chim. Acta., 47, 2425 (1964)]
2. 2). The amino acetal is a precursor of and is easier to prepare than 1-dimethylamino-1-methoxyethylene which has formerly been used for Claisen rearrangements [D. Felix, K. Gsch-wend-Steen, A. E. Wick, and A. Eschenmoser, Helv. Chim. Acta., 52, 1030 (1969)].
3. Cf. C. L. Perrin and D. J. Faulkner, Tetrahedron Letters, 2783 (1969), and ref 3b,d,e, 4, and 5 cited therein.
4. W. H. Watanabe and L. E. Conlon, J. Am. Chem. Soc., 79, 2828 (1957).
5. J. C. Collins, W. W. Hess, and F. J. Frank, Tetrahedron Letters, 3363 (1968).
6. D. J. Faulkner and M. R. Petersen, Tetrahedron Letters, 3243 (1969).
7. Cf. The synthesis of J. W. Cornforth, R. H. Cornforth, and K. K. Mathew, J. Chem. Soc., 2539 (1959), which is about 80% stereoselective for each double bond.
8. Cf. J. Fakstorp, D. Raleigh, and L. E. Schniepp, J. Am. Chem. Soc., 72, 869 (1950).
9. See W. S. Johnson, A. van der Gen, and J. J. Swoboda, J. Am. Chem. Soc., 89, 170 (1967), footnote 9.
10. K. V. Scherer, Jr., G. A. Ungefug, and R. S. Lunt, III, J. Am. Chem. Soc., 88, 2859 (1966).