Highly Stereoselective Synthesis of syn-1,3-Diols through a Sequential Titanium-Mediated Aldol Reaction and LiBH4 Reduction

✍ Scribed by Judit Esteve; Sònia Matas; Miquel Pellicena; Javier Velasco; Pedro Romea; Fèlix Urpí; Mercè Font-Bardia

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: English
• Weight: 216 KB
• Volume: 2010
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201000293

✦ Synopsis

Abstract

A sequential transformation based on a titanium‐mediated aldol reaction from chiral α‐tert‐butyldimethylsilyloxy ketones followed by reduction of the resultant aldolates with LiBH~4~ provides a straightforward access to syn‐1,3‐diols. These diols, containing up to three new stereocentres, can be easily isolated in high yields after a simple work‐up without any additional oxidative treatment, which confers to this procedure an appealing position to prepare stereoselectively such sort of structures.