Hetero-Diels-Alder reactions of α-carbonylated styrylphosphonates with enol ethers.: High-pressure influence on reactivity and diastereoselectivity

被引：15
|
作者：
Al-Badri, H
Maddaluno, J
Masson, S
Collignon, N
机构：
[1] INSA Rouen, CNRS, UPRES A6014, IRCOF,Lab Heterochim, F-76131 Mt St Aignan, France
[2] Univ Rouen, CNRS, UPRES A6014, IRCOF,Lab Fonct Azotees & Oxygenees Complexes, F-76821 Mt St Aignan, France
[3] Univ Caen, CNRS, UMR 6507, Lab Chim Mol & Thioorgan, F-14050 Caen, France
[4] IMSRA, F-14050 Caen, France
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1999年 / 16期
关键词：
D O I：
10.1039/a903972d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Variously substituted alpha-carbonylated styrylphosphonates 5 were easily prepared by Knoevenagel-type syntheses, and used as oxadienes in hetero-Diels-Alder [4 + 2] cycloadditions with enol ethers, to give new phosphonylated 3,4-dihydro-2H-pyrans 6. It was confirmed that the reactivity , as well as the trans-diastereoselectivity of the reaction, was significantly enhanced by the use of high-pressure conditions, particularly in the presence of (BuOH)-O-t as a co-solvent. Moreover, a one-pot synthesis of 6 via a tandem-sequence Knoevenagel and hetero-Diels-Alder reactions was achieved.
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页码：2255 / 2266
页数：12
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