Enantioselective radical allylation of α-iodoamides using chiral aluminum based Lewis acids

Tetrahedron Letters

Volumn 38, Issue 15, 1997, Pages 2661-2664

  Fhal, Anna Reine ^a   Renaud, Philippe ^a  

^a Institut de Chimie Organique   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE;

ALKYLATION; ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030959442     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00411-5     Document Type: Article

References (25)

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4. Recently, the first enantioselective radical reactions using chiral Lewis acids have been reported: (a) Murakata, M; Tsutsui, H.; Hoshino, O. J. Chem. Soc., Chem. Commun. 1995, 481-482.
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19. For other aluminum based chiral Lewis acids, see ref. 1b and: (a) Maruoka, K.; Itoh, T.; Shirasaka, T.; Yamamoto, H. J. Am. Chem. Soc. 1988, 110, 310-312.
20. (b) Rebiere, F.; Riant, O.; Kagan, H. B. Tetrahedron: Asymmetry 1990, 1, 199-214.
21. For a similar hydrolysis experiment, see: Sibi, M. P.; Ji, J. Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192. For the absolute configuration of (S)-2-methyl-4-pentenoic acid, see: Riley, R. G.; Silverstein, R. M. Tetrahedron 1974, 30, 1171-1174.
22. For a similar hydrolysis experiment, see: Sibi, M. P.; Ji, J. Angew. Chem. Int. Ed. Engl. 1996, 35, 190-192. For the absolute configuration of (S)-2-methyl-4-pentenoic acid, see: Riley, R. G.; Silverstein, R. M. Tetrahedron 1974, 30, 1171-1174.
23. For a leading reference on the use of metal-TADDOLate in Diels-Alder reactions, see: Seebach, D.; Dahinden, R.; Marti, R. E.; Beck, A. K.; Plattner, D. A.; Kuhnle, N. M. J. Org. Chem. 1995, 60, 1788-1799.
24. 3B in hexane (1.0 ml), dry oxygen was bubbled for 20 min. The reaction mixture was then treated with 1M NaOH according to procedure A.
25. Enantioselective direct reduction of complexed radicals has been reported, see ref. 3a. For examples dealing with radical additions to complexed activated alkenes, see ref. 3b-3e.