Atom Transfer Cyclization Reactions of α-Iodo Esters, Ketones, and Malonates: Examples of Selective 5-Exo, 6-Endo, 6-Exo, and 7-Endo Ring Closures

Journal of Organic Chemistry

Volumn 54, Issue 13, 1989, Pages 3140-3157

  Curran, Dennis P ^a   Chang, Chi tai ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

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Indexed keywords

EID: 33645559650     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00274a034     Document Type: Article

References (60)

1. Recipient of a Sloan Foundation Fellowship, 1985–87. Dreyfus Teacher-Scholar, 1985–89. Eli Lilly Grantee, 1985–87. Merck Faculty Development Awardee, 1986–87, NIH Research Carrer Development Awardee. 1987–92.
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5. Iodine atom transfer is a key step in a series of new redox chain additions to protonated heteroaromatic bases: Fontana, F.; Minisci, F.; Vismara, E. Tetrahedron Lett. 1987, 28, 6373. It is probably also an important step in recent triethylborane-promoted additions of iodides to enones: Nozaki, K.; Oshime, K.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1041.
6. Portions of this work have been reported in preliminary form. Curran, D. P.; Chang, C. T. Tetrahedron Lett. 1987, 28, 2477 and Section 5.2.2 of ref 2a.
7. Electrophilic (carbonyl-substituted) radicals have frequently been formed by the addition of nucleophilic radicals to activated alkenes but have rarely been used to form CC bonds in cyclization reactions. For examples, see: Curran, D. P.; Kuo, S. C. Tetrahedron 1987, 43, 5653. Feldman, K. S.; Romanelli, A. L.; Ruckle, R. E., Jr.; Miller, R. F. J. Am. Chem. Soc. 1988. 110. 3300. See also ref 4c.
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