A facile synthesis of chiral ω-allyl- and ω-n-propyllactones via asymmetric allylboration of formyl esters with B- allyldiisopinocampheylborane

Tetrahedron Asymmetry

Volumn 10, Issue 1, 1999, Pages 11-15

  Ramachandran, P Veeraraghavan ^a   Krzeminski, Marek P ^a   Reddy, M Venkat Ram ^a   Brown, Herbert C ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORANE DERIVATIVE; LACTONE DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; CYCLIZATION; ENANTIOMER; PRIORITY JOURNAL; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033556593     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00477-7     Document Type: Article

References (23)

1. Post-doctoral research associate on a grant from the Purdue Borane Research Fund.
2. (a) Yoda, H.; Naito, S.; Takabe, K.; Tanaka, N.; Hosoya, K. Tetrahedron Lett. 1990, 31, 7623.
3. (b) Sugiyama, T.; Muruyama, T.; Yamashita, K. Tetrahedron Lett. 1990, 31, 7343.
4. Takano, S.; Shimazaki, Y.; Lekiguchi, Y.; Ogasawara, K. Synthesis 1989, 539.
5. Sanchez-Sancho, F.; Valverde, S.; Herradon, B. Tetrahedron: Asymmetry 1996, 7, 3209.
6. Paterson, I.; Fleming, I. Tetrahedron Lett. 1979, 993.
7. Curran, D. P.; Ko, S. B. J. Org. Chem. 1994, 59, 6139.
8. Hoffmann, H. M. R.; Rabe, J. Angew. Chem., Int. Ed. Engl. 1985, 24, 94.
9. (a) Brown, H. C.; Ramachandran, P. V. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Greenwich, CT, 1995; Vol. 1, Chapter 5.
10. (b) Brown, H. C.; Ramchandran, P. V. J. Organomet. Chem. 1995, 500, 1.
11. Utaka, M.; Watasu, H.; Takeda, A. J. Org. Chem. 1987, 52, 4363.
12. Brown, H. C.; Chandrasekharan, J.; Ramachandran, P. V. J. Am. Chem. Soc. 1988,110, 1539. DIP-Chloride™ is a trademark of the Aldrich Chemical Company.
13. Ramachandran, P. V.; Chen, G. M.; Brown, H. C. Tetrahedron Lett. 1996, 37, 2205.
14. Brown, H. C.; Jadhav, P. K. J. Am. Chem. Soc. 1983, 105, 2092.
15. Brown, H. C.; Kulkarni, S. V.; Racherla, U. S. J. Org. Chem. 1994, 59, 365.
16. Methyl glyoxylate was prepared via periodate cleavage of dimethyl tartrate. Vogel, A. I. Textbook of Practical Organic Chemistry; Longman: Essex, 1989; p. 592.
17. CHIRALCEL® OD-H™ is a product of Chiral Technologies, Inc., Exton, PA.
18. Huckstep, M.; Taylor, R. J. K. Synthesis 1982, 881.
19. Bosone, E.; Farina, P.; Guazzi, G.; Innocenti, S.; Marolata, V.; Valcavi, U. Synthesis 1983, 942.
20. β-DEX 120™ is a trademark of Supelco.
21. Mukaiyama, T.; Usui, M.; Saigo, K. Chem. Lett. 1976, 49.
22. Brown, H. C.; Pai, G. G. J. Org. Chem. 1985, 50, 1384.
23. Stewart, J. D.; Reed, K. W.; Zhu, J.; Chen, G.; Kayser, M. M. J. Org. Chem. 1996, 61, 7652.