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Purification of Laboratory Chemicals, 8th Edition by W.L.F. Armarego

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MIB acts as an efficient catalyst for the enantioselective addition of the ethoxy vinyl zinc reagent to aldehydes providing hydroxy vinyl ethers, which in turn, are easily converted to chiral hydroxy aldehydes [Jeon et al. Org Lett 7 1729 2005]. It generally catalyses the addition of organo-zinc reagents (e.g. from transmetalation of allylic boranes with alkylZn compounds) to aldehydes with very high enantiomeric preference, viz (R)-MIB providing the (R)-alcohol from the corresponding aldehyde [Nugent JCS Chem Commun 1369 1999, DOI: 10.1039/A904042K; Jeon et al. Org Lett 7 1729 2005, DOI: 10.1021/ol050255n], and this catalytic method has been adopted for the preparation of α-amino acids [Chen et al. J Am Chem Soc 124 12225 2002, DOI: 10.1021/ja027271p], ...

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