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With aromatic and heteroaromatic aldehydes, the alkynylogous aldol reaction with (<jats:italic>R<\/jats:italic>)\u2010DTBM\u2010SEGPHOS as the ligand proceeded smoothly to furnish the products in excellent regioselectivity with good to high diastereoselectivity and excellent enantioselectivity. In the cases of aliphatic aldehydes, esters of but\u20102\u2010yn\u20101\u2010ol as the substrates and (<jats:italic>R<\/jats:italic>,<jats:italic>R<\/jats:italic>)\u2010Ph\u2010BPE as the ligand were found to be crucial to get good to high regio\u2010 and diastereoselectivity. The produced chiral 2,3\u2010allenols are easily transformed into synthetically useful 2\u2010furanones through cyclization. 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