Abstract
Abstract Image
Herein a new double O-directed free radical hydrostannation reaction is reported on the structurally complex dialkyldiyne 11. Through our use of a conformation-restraining acetal to help prevent stereocenter-compromising 1,5-H-atom abstraction reactions by vinyl radical intermediates, the two vinylstannanes of 10 were concurrently constructed with high stereocontrol using Ph3SnH/Et3B/O2. Distannane 10 was thereafter elaborated into the bis-vinyl iodide 9 via O-silylation and double I–Sn exchange; double Stille coupling of 9, O-desilylation, and oxidation thereafter furnished 8.
Original language | English |
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Pages (from-to) | 1168-1171 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 16 |
Issue number | 4 |
Early online date | 06 Feb 2014 |
DOIs | |
Publication status | Published - 2014 |