A convenient trans diastereoselective synthesis of 3-butadienylazetidinones and their Diels-Alder cycloaddition reactions

Arun Sharma, Sujit N. Mazumdar, Mohinder P. Mahajan

Research output: Contribution to journalArticle

46 Citations (Scopus)

Abstract

An efficient trans diastereoselective synthesis for azetidinones 3 having 3-dienyl functionalities was developed. The method first involved the [2 + 2] cycloaddition of butadienylketene with various imines 1. The 3-dienyl functionality of the resulting azetidinones 3 was then exploited in Diels-Alder cycloaddition reactions with dienophiles, viz. dimethyl acetylenedicarboxylate (DMAD), maleic anhydride (MA), N-phenylmaleimide (NPM), and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD). The reactions of 3 with DMAD and PTAD resulted in the diastereoselective synthesis of the corresponding Diels-Alder adducts 5a,b and 6. However, the reactions with MA and NPM yielded a mixture (2:1) of diastereoisomers 7/7' and 8/8'.

Original languageEnglish (US)
Pages (from-to)5506-5509
Number of pages4
JournalJournal of Organic Chemistry
Volume61
Issue number16
DOIs
StatePublished - Aug 9 1996

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Maleic Anhydrides
Cycloaddition
Imines
N-phenylmaleimide
2-azetidinone
4-phenyl-1,2,4-triazoline-3,5-dione
acetylenedicarboxylic acid dimethyl ester

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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title = "A convenient trans diastereoselective synthesis of 3-butadienylazetidinones and their Diels-Alder cycloaddition reactions",
abstract = "An efficient trans diastereoselective synthesis for azetidinones 3 having 3-dienyl functionalities was developed. The method first involved the [2 + 2] cycloaddition of butadienylketene with various imines 1. The 3-dienyl functionality of the resulting azetidinones 3 was then exploited in Diels-Alder cycloaddition reactions with dienophiles, viz. dimethyl acetylenedicarboxylate (DMAD), maleic anhydride (MA), N-phenylmaleimide (NPM), and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD). The reactions of 3 with DMAD and PTAD resulted in the diastereoselective synthesis of the corresponding Diels-Alder adducts 5a,b and 6. However, the reactions with MA and NPM yielded a mixture (2:1) of diastereoisomers 7/7' and 8/8'.",
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A convenient trans diastereoselective synthesis of 3-butadienylazetidinones and their Diels-Alder cycloaddition reactions. / Sharma, Arun; Mazumdar, Sujit N.; Mahajan, Mohinder P.

In: Journal of Organic Chemistry, Vol. 61, No. 16, 09.08.1996, p. 5506-5509.

Research output: Contribution to journalArticle

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AB - An efficient trans diastereoselective synthesis for azetidinones 3 having 3-dienyl functionalities was developed. The method first involved the [2 + 2] cycloaddition of butadienylketene with various imines 1. The 3-dienyl functionality of the resulting azetidinones 3 was then exploited in Diels-Alder cycloaddition reactions with dienophiles, viz. dimethyl acetylenedicarboxylate (DMAD), maleic anhydride (MA), N-phenylmaleimide (NPM), and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD). The reactions of 3 with DMAD and PTAD resulted in the diastereoselective synthesis of the corresponding Diels-Alder adducts 5a,b and 6. However, the reactions with MA and NPM yielded a mixture (2:1) of diastereoisomers 7/7' and 8/8'.

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