NDLI: Stereoselectivity of Intramolecular Diels-Alder Reaction of Hydroxamate-Tethered 1,3,9-Decatrienes under Thermal and Microwave Heating

Content Provider	Semantic Scholar
Author	Wang, Yan Guo Wu, Jinlong
Copyright Year	2009
Abstract	Intramolecular Diets-Alder (IMDA) reaction of the hydroxamate-tethered 1,3,9-decatrienes has been investigated under both thermal and microwave heating, and the stereoselectivity has been revisited. It was found that a temperature-dependent rearrangement of (2E,4E)-hexadien-1-yl N-benzylhydroxamates into the corresponding (2E,4)-1-methylpentadien-1-yl derivatives took place prior to IMDA reaction upon heating, and up to four cycloadducts were identified by analysis of the crude reaction mixtures. The IMDA reaction could be accelerated with microwave irradiation at 180 °C in MeCN. Stereoselectivity of the microwave-assisted IMDA reaction has been examined by using the substituents appended at C1, C5, and C 10 of the hydroxamate-tethered 1,3,9-decatrienes.
Starting Page	2862
Ending Page	2866
Page Count	5
File Format	PDF HTM / HTML
DOI	10.1055/s-0029-1217966
Volume Number	2009
Alternate Webpage(s)	https://www.thieme-connect.com/media/synlett/200917/supmat/sup_w10609st-10-1055_s-0029-1217966.pdf
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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