Investigation of the hydroxyl directing effect on the Paternò-Büchi reaction on 5-(2-triisopropylsilyloxazolyl)methanol derivatives

详细信息    查看全文

• 作者：Maurizio D'Auria ; ^{maurizio.dauria@unibas.it" class="auth_mail" title="E-mail the corresponding author} ; Rocco Racioppi ; Federico Rofrano ; Sonia Stoia ; Licia Viggiani
• 关键词：Paternò ; &ndash ; Bü ; chi reaction ; Oxazole ; 5-Oxazolylmethanol derivatives ; Hydroxyl directing effect ; DFT calculations ; Conformations
• 刊名：Tetrahedron
• 出版年：2016
• 出版时间：18 August 2016
• 年：2016
• 卷：72
• 期：33
• 页码：5142-5148
• 全文大小：944 K

文摘

The photochemical coupling of 5-oxazoylmethanol derivatives with benzophenone and benzaldehyde showed that the hydroxyl directing effect in the Paternò–Büchi reaction described in the case of allylic alcohols and furylmethanol derivatives can also be present in the case of 5-oxazolylmethanol derivatives. In this case, the reaction with aromatic aldehydes showed an unusual endo stereoselectivity. The observed stereoselectivity can be predicted on the basis of the interaction between HSOMO and LSOMO in the biradical intermediate.