o-(Hydroxyalkyl)phenyl P-Chirogenic Phosphines as Functional Chiral Lewis Bases

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• 作者：Emmanuelle R茅mond ; J茅r么me Bayardon ; Shinobu Takizawa ; Yoann Rousselin ; Hiroaki Sasai ; Sylvain Jug茅
• 刊名：Organic Letters
• 出版年：2013
• 出版时间：April 19, 2013
• 年：2013
• 卷：15
• 期：8
• 页码：1870-1873
• 全文大小：267K
• 年卷期：v.15,no.8(April 19, 2013)
• ISSN：1523-7052

文摘

The stereoselective synthesis of P-chirogenic phosphines bearing an o-hydroxyalkyl chelating arm is described. The synthesis is based either on the hydroxyalkylation of P-chirogenic o-bromophenylphosphines (borane) or on their carbonatation and then reduction. The hydroxyalkylation with benzaldehyde or pivalaldehyde affords a mixture of epimers which are isolated by chromatography and characterized by their X-ray structures. Preliminary assays of free P-chirogenic o-(hydroxyalkyl)phenyl phosphines, as new functional Lewis bases in catalyzed asymmetric aza-MBH reaction, lead to 尾-aminoester derivatives with ee values up to 74%.