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2005
Alkynes
Q 0087
16- 071
Meerwein—Ponndorf—Verley Alkynylation of Aldehydes: Essential Modification of Aluminum Alkoxides for Rate Acceleration and Asymmetric Synthesis.
— The present new Meerwein—Ponndorf—Verley alkynylation of aldehydes proceeds
without alkynyl metal reagents under mild conditions. Best results are achieved using
3 equiv. of alkynes. In some cases, alkynylation can also be performed with a catalytic
amount of aluminum alkoxide, but longer reaction times are required. For the asymmetric reaction, a new axially chiral biphenol ligand is used which in situ forms a conformationally flexible aluminum alkoxide. The method is limited to reactive aldehydes.
— (OOI, T.; MIURA, T.; OHMATSU, K.; SAITO, A.; MARUOKA*, K.; Org.
Biomol. Chem. 2 (2004) 22, 3312-3319; Dep. Chem., Grad. Sch. Sci., Kyoto Univ.,
Sakyo, Kyoto 606, Japan; Eng.) — S. Adam
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