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2005
Araliphatic ethers
Q 0290
Catalytic Reductive Coupling of Epoxides and Aldehydes: Epoxide-Ring Opening
Carbonyl Reduction. — The reductive ring opening reaction of terminal
16- 075 Precedes
epoxides (I) with aldehydes (II) proceeds smoothly in the presence of the common catalyst RhCl(PPh3)3 to furnish the β-hydroxy ethers in good yields. The addition of triethylamine is necessary for sterically encumbered aldehydes. This is the first use of
Et3B as reductant in the presence of Wilkinson catalyst. The reaction can be applied to
acid-labile substrates like (IV). Aromatic hydroxy groups are inactive and only the
aldehyde reacts in substrate (VI). An enantiopure epoxide (VIII) reacts with complete
retention of configuration. — (MOLINARO, C.; JAMISON*, T. F.; Angew. Chem.,
Int. Ed. 44 (2005) 1, 129-132; Dep. Chem., MIT, Cambridge, MA 02139, USA; Eng.)
— Mischke
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