Enantiopure Acetals of α-Alkynyl Carbonyl Compounds: Organoaluminum-Mediated 1,2-Shift of Cobalt-Complexed Alkynyl Group with Concomitant Capture by a Nucleophile

Synlett

Volumn 1997, Issue 3, 1997, Pages 304-306

  Taya, Kimiko ^a   Nagasawa, Tetsuya ^a   Suzuki, Keisuke ^a,b  

^a KEIO UNIVERSITY   (Japan)

^b TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003103121     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-776     Document Type: Article

References (9)

1. Nagasawa, T.; Taya, K.; Kitamura, M.; Suzuki, K. J. Am. Chem. Soc. 1996, 118, 8949.
2. a) Nicholas, K. M. Acc. Chem. Res. 1987,20, 207;
3. b) Schreiber, S. L.; Klimas, M. T.; Sammakia, T. J. Am. Chem. Soc. 1987, 109, 5749.
4. Honda, Y.; Ori, A.; Tsuchihashi, G. Chem. Lett. 1986, 13; Honda, Y.; Morita, E.; Tsuchihashi, G. Chem. Lett. 1986, 277.
5. Honda, Y.; Ori, A.; Tsuchihashi, G. Chem. Lett. 1986, 13; Honda, Y.; Morita, E.; Tsuchihashi, G. Chem. Lett. 1986, 277.
6. Mesylate 6 was prepared as follows. For the starting D-lactamide derivative, see Suzuki, K.; Tomooka, K.; Katayama, E.; Matsumoto, T.; Tsuchihashi, G. J. Am. Chem. Soc. 1986, 108, 5221. (Matrix Presented)
7. For a review on organoaluminum reagents, see Maruoka, K.; Yamamoto, H. Tetrahedron 1988, 44, 5001.
8. 3a) 87.3, 88.8 87.3 a) Note that the triple bond is saturated. The e.e. of acetals 10 and 14 was determined by GC analysis (Chiral-DEX CB, CHROMPACK, vide supra) of compound 19 (1:1-diastereomeric mixture) derived from 10 by allylation and decomplexation. Peaks for 19 (oven temp.: 150°C; column pressure: 100 kPa; split flow: 80 mL/min.) appeared at 12.1 and 12.4 min. Cf. The racemate showed peaks at 11.9, 12.1, 12.2 and 12.4 min. (Matrix Presented)
9. Seyferth, D.; Wehman, A. T. J. Am. Chem. Soc. 1970, 92, 5520.