“…The selectivity is explained in the standard manner through the intervention of a Beckwith, chairlike transition state. Related examples in which the SO 2 Ph group was replaced by CO 2 Me behaved similarly. , 96 …”
Section: Cyclizations Of 5-hexenoyl Radicalsmentioning
“…The selectivity is explained in the standard manner through the intervention of a Beckwith, chairlike transition state. Related examples in which the SO 2 Ph group was replaced by CO 2 Me behaved similarly. , 96 …”
Section: Cyclizations Of 5-hexenoyl Radicalsmentioning
“…Acyl selenides and selenol esters can produce acyl radicals under mild conditions, which can be used in a large variety of inter-and intramolecular reactions [5]. Acyl selenides are also well known for their liquid crystalline properties [6].…”
“…Methods that utilize acyl radicals have, however, not been forthcoming. In this paper, we describe the first example of the intramolecular addition of an acyl radical to a vinylogous carbonate for the efficient and stereoselective construction of 5-, 6-, and 7-membered cyclic ethers (eq 1) …”
Cyclic ether containing natural products represent important synthetic targets owing to their unique structural and biological properties. 1 The development of new methodology for the synthesis of this ubiquitous class of compounds has been the focus of extensive investigation for the last 20 years. However, the development of new and general methods capable of accessing this class of compounds continues to dominate this area of investigation. 2 A number of radical methods 3-5 have recently been developed for the stereoselective synthesis of cyclic ethers. Methods that utilize acyl radicals 6 have, however, not been forthcoming. In this paper, we describe the first example of the intramolecular addition of an acyl radical to a vinylogous carbonate for the efficient and stereoselective construction of 5-, 6-, and 7-membered cyclic ethers (eq 1). 7
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