Asymmetric cyclopropanation reaction under phase-transfer catalyzed conditions

Tetrahedron Letters

Volumn 40, Issue 22, 1999, Pages 4215-4218

  Arai, Shigeru ^a   Nakayama, Keiji ^a   Ishida, Toshimasa ^b   Shioiri, Takayuki ^a  

^a NAGOYA CITY UNIVERSITY   (Japan)

^b OSAKA MEDICAL COLLEGE   (Japan)

Author keywords

Asymmetric reactions; Catalysts; Cyclopropanes; Phase transfer

Indexed keywords

AMINE; CYCLOPROPANE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; PHASE TRANSITION; PROTON TRANSPORT; STEREOISOMERISM;

EID: 0033612173     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00679-6     Document Type: Article

References (13)

1. For recent books on PTC, see (a) Phase-transfer Catalysis. Mechanism and Syntheses; Halpern, M. E., Ed.; American Chemical Society, Washington, D C, 1997.
2. (b) Handbook of Phase Transfer Catalysis; Sasson, Y; Neumann, R. Ed.; Blackie A. & M., London, 1997.
3. (a) Arai, S.; Shioiri, T. Tetrahedron Lett. 1998, 39, 2145-2148.
4. (b) Arai, S.; Tsuge, H.; Shioiri, T. Tetrahedron Lett. 1998, 39, 7563-7566.
5. (a) Arai, S.; Nakayama, K.; Hatano, K.; Shioiri, T. J. Org. Chem. 1998, 54, 9572-9575.
6. (b) Arai, S.; Suzuki, Y.; Nakayama, K.; Hatano, K.; Shioiri, T. Tetrahedron Lett. 1998, 39, 9739-9742.
7. (a) Kowalski, C.; Weber, A. E.; Fields, K. W. J. Org. Chem. 1982, 47, 5088-5093.
8. (b) Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Tetrahedron Lett. 1992, 33, 917-918. Other types of enones such as α-chloro or iodocycloalkenone gave 2a in lower yield and ee.
9. Ono, S.; Kaji, A. Synthesis 1986, 693-704.
10. (a) Mash, E. A.; Nelson, K. A. Tetrahedron 1987, 43, 679-692.
11. 3).
12. 3) (83% ee); Enantiomeric excess was determined by HPLC analysis (DAICEL CHIRALCEL OD, hexane:i-PrOH = 9:1, flow rate =1.0 mL/min). The retention times were 21.6 min (major) and 24.9 min (minor), respectively.
13. The absolute configurations of 2b, 2d, and 2e were tentatively assigned as described in Tables 2 and 3 due to both their sign of optical rotation and the behavior observed in HPLC analysis.