1,13 and 1,14 asymmetric induction: Remote control

✍ Scribed by Nicholas Magnus; Philip Magnus

• Book ID: 104257066
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 176 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)00704-1

✦ Synopsis

Treatment of the acyclic sulfones 6 (n = 1, 2, 3 and 4) with n-BuLI/THF/-100°C followed by PhCHO gave only two diastereomeric ~-hydroxysulfones 7. The selection of two out of a possible four diastereomers is observed even though the chiral inducing entity is 10, 11, 12 and 13 atoms from the reaction locus. These results represent the illustration of long range asymmetric induction (LAI) controlled by supramolecular interactions.