TY - JOUR
T1 - [3 + 2] Cycloadditions of carbonyl oxides to imines
T2 - An alternative approach to the synthesis of 1,2,4-dioxazolidines
AU - McCullough, Kevin J.
AU - Mori, Mitsuyuki
AU - Tabuchi, Toshihiko
AU - Yamakoshi, Hideyuki
AU - Kusabayashi, Shigekazu
AU - Nojima, Masatomo
PY - 1995
Y1 - 1995
N2 - Carbonyl oxides, derived from the ozonolysis of vinyl ethers, readily undergo [3 + 2] cycloadditions with imines, affording the corresponding 1,2,4-dioxazolidines 6a-z in the isolated yields of 14-97%. High degrees of stereoselectivity are observed in certain cases, suggesting that this [3 + 2] cycloaddition proceeds by a concerted process. In competition experiments, a relative order of reactivity towards carbonyl oxides was tentatively deduced: nitrone > imine > thioketone > carbonyl compound. The structure of the 1,2,4-dioxazolidine 6d was unambiguously determined by the X-ray crystallographic analysis. 1,2,4-Dioxazolidines were found to undergo ring cleavage reactions on either thermolysis or treatment with base.
AB - Carbonyl oxides, derived from the ozonolysis of vinyl ethers, readily undergo [3 + 2] cycloadditions with imines, affording the corresponding 1,2,4-dioxazolidines 6a-z in the isolated yields of 14-97%. High degrees of stereoselectivity are observed in certain cases, suggesting that this [3 + 2] cycloaddition proceeds by a concerted process. In competition experiments, a relative order of reactivity towards carbonyl oxides was tentatively deduced: nitrone > imine > thioketone > carbonyl compound. The structure of the 1,2,4-dioxazolidine 6d was unambiguously determined by the X-ray crystallographic analysis. 1,2,4-Dioxazolidines were found to undergo ring cleavage reactions on either thermolysis or treatment with base.
UR - http://www.scopus.com/inward/record.url?scp=37049066954&partnerID=8YFLogxK
M3 - Article
SN - 1472-7781
SP - 41
EP - 48
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
IS - 1
ER -