A mild method for generation of p-methoxybenzyl cation through NIS-mediated activation of p-methoxybenzyl 4-pentenyl ether

Tetrahedron

Volumn 52, Issue 24, 1996, Pages 8135-8142

  Okada, Midori ^a,b   Kitagawa, Osamu ^b   Fujita, Masao ^b   Taguchi, Takeo ^b  

^a TOKYO WOMEN'S MEDICAL UNIVERSITY   (Japan)

^b TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATION;

ALCOHOL METABOLISM; ANALYTIC METHOD; ARTICLE; CATION TRANSPORT; CHEMICAL REACTION KINETICS; DRUG MECHANISM; MOLECULAR DYNAMICS; PRIORITY JOURNAL;

EID: 0029887425     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00375-4     Document Type: Article

References (15)

1. Rychnovsky, S.; Bartlett, P. A. J. Am. Chem. Soc. 1981, 103, 3963-3964.
2. Useful glycosidation and hydrolysis through the activation of 4-pentenylglycoside by electrophilic halogenating reagent were reported by Fraser-Reid et al., a) Fraser-Reid, B.; Konradsson, P.; Mootoo, D. R.; Uododong, U. J. Chem. Soc., Chem. Commun, 1988, 823-824.
3. b) Mootoo, D. R.; Date, V.; Fraser-Reid, B. J. Am. Chem. Soc., 1988, 110, 2662-2663.
4. For our recent studies on α-iodination reaction and Diels-Alder reaction of amides and lactams through iodine-mediated activating process, a) Kitagawa, O.; Hanano, T.; Hirata, H.; Inoue, T.; Taguchi, T. Tetrahedron Lett., 1992, 33, 1299-1302.
5. b) Kitagawa, O.; Hanano, T.; Kikuchi, N.; Taguchi, T. Tetrahedron Lett., 1993, 34, 2165-2168.
6. c) Kitagawa, O.; Aoki, K.; Inoue, T.; Taguchi, T. Tetrahedron Lett., 1995, 36, 593-596.
7. d) Kitagawa, O.; Kikuchi, N.; Hanano, T.; Aoki, K.; Yamazaki, T.; Okada, M.; Taguchi, T. J. Org. Chem., 1995, 60, 7161-7165.
8. a) Horita, K.; Yoshioka, T.; Tanaka, T.; Oikawa, Y.; Yonemitsu, O. Tetrahedron, 1986, 42, 3021-3028.
9. b) Yonemitsu, O.; Nakajima, N. Hikota, M. J. Syn. Org. Chem. Jpn., 1990, 48, 102-118.
10. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, John Wiley and Sons, Inc.: New York, 1991; pp 53-56 and references cited therein.
11. Nakajima, N.; Horita, K.; Abe, R.; Yonemitsu, O. Tetrahedron Lett., 1988, 29, 4139-4142. See also ref. 5.
12. 4 reduction of 3f.
13. A synthesis of cyclic ether through the formation of p-methoxybenzyl cation. Noda, I.; Horita, K.; Oikawa, Y.; Yonemitsu, O. Tetrahedron Lett., 1986, 27, 1917-1920.
14. 2Zn to anisaldehyde using a chiral aminoalcohol. Soai, K.; Ookawa, T.; Kaba, T.; Ogawa, K. J. Am. Chem. Soc., 1987, 109, 7111-7121.
15. The ee of 11 and 12 was determined by HPLC analysis using Daicel CHIRALCEL OD column (4.6 × 250 mm; detection, 254-nm UV light). 11: eluent, 3% 2-propanol in hexane; flow rate, 1.0 ml/min; retention time (min), R isomer 18.5, S isomer 20.5. 12: 0.1 % AcOEt in hexane; 1.0 ml/min; S isomer 8.9, R isomer 10.0.