Rhodium-Catalyzed Asymmetric Ring Opening of Oxabicyclic Alkenes with Sulfur Nucleophiles
- 13 February 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (6) , 2194-2196
- https://doi.org/10.1021/jo035730e
Abstract
The synthesis of 2-sulfanyl-1,2-dihydro-naphthalen-1-ols is described. This methodology is based on rhodium catalysis and enables various thiols to undergo an asymmetric SN2' ring opening of oxabenzonorbornadiene. Under the reaction conditions ([Rh(COD)Cl](2) (2.5 mol %), (S)-(R)-PPF-P(t)Bu(2) (6 mol %), AgOTf (7 mol %), NH(4)I (1.7 equiv), galvinoxyl (5 mol %), THF, 85 degrees C), aryl- and alkyl-sulfide adducts are obtained in good to excellent yield and in high enantiomeric excess (>90% ee).Keywords
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