Chemoselective intramolecular aminocarbonylation of unsaturated amides under Wacker-type conditions

Tetrahedron Letters

Volumn 37, Issue 40, 1996, Pages 7287-7290

  Harayama, Hiroto ^a   Okuno, Hirofumi ^a   Takahashi, Yoshika ^a   Kimura, Masanari ^a   Fugami, Keigo ^a   Tanaka, Shuji ^a   Tamaru, Yoshinao ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; BETA AMINO ACID;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030607226     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01650-4     Document Type: Article

References (10)

1. 1. Hegedus, L. S. Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, U.K., 1991; Vol. 4, pp. 559-563.
2. 2. The terms exo and endo used here are to discriminate two types of nitrogen nucleophiles: for example, exo-carbamates (1a) are meant to refer to those providing nitrogen neterocycles (e.g., 2a, eq 1) that possess the carbamate group as the ring substituent and endo-carbamates (3) are those furnishing heterocycles that contain the carbamate group as the ring component (e.g., 4, eq 2).
3. 3. (a) Tamara, Y.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5731-5741.
4. (b) Tamaru, Y.; Hojo, M.; Higashimura, J.; Yoshida, Z. J. Am. Chem. Soc. 1988, 110, 3994-4002.
5. 4. (a) Kimura, M.; Saeki, N.; Uchida, S.; Harayama, H.; Tanaka, S.; Fugami, K.; Tamara, Y. Tetrahedron Lett. 1993, 34, 7611-7614.
6. (b) Tamaru, Y.; Tanigawa, H.; Itoh, S.; Kimura, M.; Tanaka, S.; Fugami, K.; Sekiyama, T.; Yoshida, Z. ibid. 1992, 33, 631-634.
7. 5. Estimated pKa of 3 is 4.2: Taylor, L. D.; MacDonald, R. J.; Rubin, E. L. J. Polym. Sci. Part A-1, 1971, 9, 3059-3063.
8. 3b
9. 7. For the similar cis selective cyclization, see ref. 3a. See also, Tamaru, Y.; Harayama, H.; Bando, T.; Nagaoka, H.; Yoshida, Z. Liebigs Ann. 1996, 223-234 and references cited therein.
10. 2: calcd. C 51.76, H 5.13, N 5.49, S 12.55; found C 51.57, H 5.05, N 5.35, S 12.73.