The Paterno-Buchi reaction-Mechanisms and application to organic synthesis

被引：89

作者：

Freneau, Maxime ^{[1
]}

Hoffmann, Norbert ^{[1
]}

机构：

[1] Univ Reims, CNRS, ICMR, Equipe Photochim,UFR Sci, BP 1039, F-51687 Reims, France

来源：

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY C-PHOTOCHEMISTRY REVIEWS | 2017年 / 33卷

关键词：

Photocycloadditions; Oxetanes; Reaction mechanism; Stereoselectivity; Organic synthesis; CARBONYL PHOTOCYCLOADDITION REACTION; ARENECARBOXYLIC ACID-ESTERS; 2+2 CYCLO-ADDITION; N-ACYL ENAMINES; PHOTOCHEMICAL-REACTIONS; OXETANE FORMATION; CHIRAL INDUCTION; HYDROGEN ABSTRACTION; ELECTRON-TRANSFER; FACIAL DIASTEREOSELECTIVITY;

D O I：

10.1016/j.jphotochemrev.2017.10.002

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The [2+2] photocycloaddition between an electronically excited carbonyl compound and an alkene leading to oxetanes (Paterno-Buchi reaction) is one of the most investigated organic photochemical reaction. Regio-, stereo- and site selectivities are discussed as a consequence of the reaction mechanism. Spin multiplicity and electron transfer have a significant impact on the outcome of the reaction. Typical carbonyl and alkene reaction partners are presented indicating scope and limitation of the reaction. The Paterno-Buchi reaction possesses particular interest for being applied to organic synthesis, considering the difficulty for non-photochemical reactions to obtain oxetanes, with or without stereoselectivity. Mechanistic details are particularly focused. It has been applied as key step in various multi-step syntheses. (C) 2017 Elsevier B.V. All rights reserved.

引用

页码：83 / 108

页数：26

共 183 条

[1] Mechanism of stereo- and regioselectivity in the Paterno-Buchi reaction of furan derivatives with aromatic carbonyl compounds: Importance of the conformational distribution in the intermediary triplet 1,4-diradicals [J].

Abe, M ;

Kawakami, T ;

Ohata, S ;

Nozaki, K ;

Nojima, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (09) :2838-2846

[2] A stereoselective, tandem [2+2] photocycloaddition-hydrolysis route to aldol-type adducts [J].

Abe, M ;

Ikeda, M ;

Nojima, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (19) :3261-3266

[3] Regio- and stereo-selective formation of 2-siloxy-2-alkoxyoxetanes in the photoreaction of cyclic ketene silyl acetals with 2-naphthaldehyde and their transformation to aldol-type adducts [J].

Abe, M ;

Ikeda, M ;

Shirodai, Y ;

Nojima, M .

TETRAHEDRON LETTERS, 1996, 37 (33) :5901-5904

[4] Paterno-Buchi photocyclization of 2-siloxyfurans and carbonyl compounds.: Notable substituent and carbonyl (aldehyde vs ketone and singlet- vs triplet-excited state) effects on the regioselectivity (double-bond selection) in the formation of bicyclic exo-oxetanes [J].

Abe, M ;

Torii, E ;

Nojima, M .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (11) :3426-3431

[5]

Abe M., 2004, CRC HDB ORGANIC PHOT

[6]

Abe M., 2010, Handbook of Synthetic Photochemistry, P217

[7] Unusual temperature dependence in the cis/trans-oxetane formation discloses competitive syn versus anti attack for the Paterno-Buchi reaction of triplet-excited ketones with cis- and trans-cyclooctenes.: Conformational control of diastereoselectivity in the cyclization and cleavage of preoxetane diradicals [J].

Adam, W ;

Stegmann, VR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (14) :3600-3607

[8] Unusual temperature-dependent diastereoselectivity in the [2+2] photocycloaddition (Paterno-Buchi reaction) of benzophenone to cis- and trans-cyclooctene through conformational control [J].

Adam, W ;

Stegmann, VR ;

Weinkötz, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (10) :2452-2453

[9] Hydroxy-directed regio- and diastereoselective [2+2] photocycloaddition (Paterno-Buchi reaction) of benzophenone to chiral allylic alcohols [J].

Adam, W ;

Peters, K ;

Peters, EM ;

Stegmann, VR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (12) :2958-2959

[10]

Albini A., 2010, Handbook of synthetic photochemistry

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