Remarkable long range effects on the diastereoface selectivity in an aldol condensation

Tetrahedron Letters

Volumn 40, Issue 12, 1999, Pages 2267-2270

  Harris, Christina R ^a   Kuduk, Scott D ^a   Balog, Aaron ^c   Savin, Ken A ^d   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

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

^c BRISTOL MYERS SQUIBB   (United States)

^d ELI LILLY AND COMPANY   (United States)

Author keywords

Aldol; Anti Cram; Epothilone B

Indexed keywords

12,13 DESOXYEPOTHILONE B; ALDOL; EPOTHILONE B; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CONFORMATION; GENETIC LINKAGE; MOLECULAR INTERACTION; NONHUMAN; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033583269     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00222-1     Document Type: Article

References (8)

1. 3 Balog, A.; Harris, C. R.; Savin, K.; Zhang, X.-G.; Chou, T. C.; Danishefsky, S. J. Angew. Chem., Int. Ed. Engl. 1998, 37, 2675-2678.
2. 4 Harris, C. R.; Kuduk, S. D.; Savin, K.; Balog, A.; Danishefsky, S. J. Tetrahedron Lett. 1999, 40, 2263.
3. 5 Heathcock, C. H. In "Asymmetric Synthesis," J. D. Morrison, Ed., 1984, Academic Press, Inc.: New York, Vol. 3, pp. 111-213.
4. 6 a.) Mukaiyama, T. Org. React. 1982, 28, 203.
5. b.) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1
6. 7 Roush, W. R. J. Org. Chem. 1991, 56, 4151-4157.
7. 8 Heathcock, C. H.; Buse, C. T.; Kleschick, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066.
8. 9 An alternate view, suggested by a reviewer of this manuscript, postulates that the unsaturation acts as a ligand on a second lithium atom complexed to the aldehyde group. We thank the referee for proposing this argument.