Generation and reaction of an oxiranyl anion derived from α,β-epoxy-γ-butyrolactone

Tetrahedron Letters

Volumn 40, Issue 41, 1999, Pages 7367-7370

  Kuramochi, Kouji ^a   Itaya, Hideyoshi ^a   Nagata, Seigo ^a   Takao, Ken Ichi ^a   Kobayashi, Susumu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Angelica lactone epoxide; Epolactaene; Fluoride catalyzed aldol reaction; Oxiranyl anion

Indexed keywords

ALDEHYDE; ANION; GAMMA BUTYROLACTONE DERIVATIVE; LACTONE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; POLYMERIZATION; REACTION ANALYSIS;

EID: 0033536609     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01511-7     Document Type: Article

References (16)

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12. 1H NMR (270 MHz) spectra are as follows: 4: δ 0.22 (9H, s), 1.35 (3H, d, J=6.6 Hz), 3.72 (1H, s), 4.69 (1H, q, J=6.6 Hz). 7: δ 0.21 (9H, s), 1.47 (3H, d, J=6.6 Hz), 3.83 (1H, d, J=1.7 Hz), 4.54 (1H, dq, J=1.7, 6.6 Hz).
13. 9. Dubuffet, T.; Sauvetre, R.; Normant, J. F. Tetrahedron Lett. 1988, 29, 5923-5924.
14. 2O present in commercial THF solution of TBAF. We found that the addition of molecular sieves 3A instead of 4A was not effective affording 6% of 10e and 78% of the recovered 4.
15. 11. Without purification and separation, the crude mixture (4, aldehyde, and 9) was retreated with TBAF and MS4A, and this operation was repeated.
16. 12. Noyori, R.; Nishida, I.; Sakata, J. J. Am. Chem. Soc. 1981, 103, 2106-2108.