One-Pot Process That Efficiently Generates Single Stereoisomers of 1,3-Bisphosphinylpropanes Having Five Chiral Centers

• Published in: Organic letters Vol. 17; no. 1; pp. 142 - 145
• Main Authors: Zhang, He, Sun, Yong-Ming, Zhao, Yalei, Zhou, Zhong-Yang, Wang, Ji-Ping, Xin, Nana, Nie, Shao-Zhen, Zhao, Chang-Qiu, Han, Li-Biao
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 02.01.2015; Amer Chemical Soc
• Subjects: Aldehydes - chemistry; Catalysis; Chemistry; Chemistry, Organic; Magnetic Resonance Spectroscopy; Molecular Structure; Phosphinic Acids - chemical synthesis; Phosphinic Acids - chemistry; Physical Sciences; Propane - analogs & derivatives; Propane - chemical synthesis; Propane - chemistry; Science & Technology; Stereoisomerism; KETONES; ACID; LIGANDS; SULFIDES; STEREOCHEMISTRY; BONDS; ASYMMETRIC HYDROGENATION; PHOSPHINE OXIDES; TERTIARY
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol503371r

P,C-Stereogenic 1,3-bisphosphinylpropanes 3 that have up to five stereogenic centers could be obtained stereoselectively in high yields by a one-step reaction of (R P)-menthylphenylphosphine oxide 1 with α,β-unsaturated aldehydes 2 catalyzed by KOH at room temperature. A mechanism was proposed as to involve a stereoselective intermolecular 1,3′-phosphorus migration from the 1,2-adduct of 1 with 2 to another 2 generating a 1,4-adduct that subsequently reacts with 1 to produce 3.