Unexpected Syn Hydride Migration in the Non-aldol Aldol Reaction

Organic Letters

Volumn 5, Issue 19, 2003, Pages 3375-3378

  Jung, Michael E ^a   Van Den Heuvel, Alexandra ^a   Leach, Andrew G ^a   Houk, K N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; CARBOCATION; ETHER DERIVATIVE; KETONE DERIVATIVE; SYN HYDRIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CALCULATION; CHEMICAL REACTION; MIGRATION; REACTION ANALYSIS; STEREOSPECIFICITY;

ALDEHYDES; EPOXY COMPOUNDS; ETHER, ETHYL; HEXANONES; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; STEREOISOMERISM;

EID: 0345255697     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0350801     Document Type: Article

References (8)

1. Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1993, 115, 12208-12209.
2. For a review, see: Pfenninger, A. Synthesis 1986, 89-116.
3. Jung, M. E.; van den Heuvel, A. Tetrahedron Lett. 2002, 43, 8169-8172.
4. Compounds 8a, 8b, and 15 were desilylated, and the NMRs of the resulting keto alcohols matched those in the literature: Hoffmann, R. W.; Ditrich, K.; Fröch, S. Liebigs Ann. Chem. 1987, 977-985.
5. (a) Sreekumar, C.; Darst, K. P.; Still, W. C. J. Org. Chem. 1980, 45, 5, 4260-4262.
6. (b) Jung, M. E.; Fahr, B. T.; D'Amico, D. C. J. Org. Chem. 1998, 63, 2982-2987.
7. Mitsunobu, O. Synthesis 1981, 1-28.
8. Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1995, 117, 7379-7380.