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[4+2] Cycloaddition of 1-phosphono-1,3-butadiene with azo- and nitroso-heterodienophiles

โœ Scribed by Jean-Christophe Monbaliu; Jacqueline Marchand-Brynaert

Publisher
Elsevier Science
Year
2008
Tongue
French
Weight
120 KB
Volume
49
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Under microwave activation, diethyl 1-phosphono-1,3-butadiene (1) reacted with t-butyl azodicarboxylate (2) and o-nitrosotoluene (5) to furnish quantitatively [4+2] cycloadducts, 3-phosphono-3,6-dihydro-1,2-pyridazine (3) and 6-phosphono-3,6-dihydro-1,2-oxazine (6), respectively. Selective oxidation and/or reduction of 6 led to functionalized d-aminophosphonic derivatives in cyclic (7, 8) and aliphatic series (9, 10). Intermediate 10 may be cyclized into 2-phosphono-2,5-dihydro-1-pyrrole (12).

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Chiral 1-phosphonodienes bearing a bicyclic (R,R)-1,3,2-dioxaphospholane or a (R,R)-1,3,2-diazaphospholidine auxiliary are potent dienes for asymmetric hetero Diels-Alder reactions. Their reactivity towards model nitroso and azodicarboxylate dienophiles has been studied by means of theoretical chemi

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cycloaddition reactions of I-aryl-4-dimethylamino-1,3diaza-1,3-butadienes (~),l-aryl-4-dimethylamino-2-methylthio-l,3-diaza-l,3butadienes 12). l-aryl-4-methylthio-2-phenyl-4-sec.amino-l,3-diaza-l,3butadienes ( 2) and 4, 4-bis~sec.amino~-l,2-diphenyl-l,3-diaza-l,3-bu~adienes 112) with monophenylketen