TY - JOUR
T1 - Highly Z/E stereoselective approach to β-iodo aza Morita-Baylis-Hillman adducts
AU - Timmons, Cody
AU - Kattuboina, Adiseshu
AU - Banerjee, Soham
AU - Li, Guigen
N1 - Funding Information:
We gratefully acknowledge financial support from the National Institutes of Health (CA 99995-1) and the Robert A. Welch Foundation (D-1361). S.B. thanks the Welch Summer Scholar Program for support.
PY - 2006/7/24
Y1 - 2006/7/24
N2 - A multicomponent reaction between sulfonyl-protected imines, magnesium iodide, and acetylenic esters or ketones is described. The resulting β-iodo aza Morita-Baylis-Hillman adducts were obtained in good yields and excellent Z/E stereoselectivities. The reaction showed good tolerance for sulfonyl protecting groups, as well as for acetylenic ketones and esters. This work presents the first synthetic approach to β-iodo aza Morita-Baylis-Hillman adducts.
AB - A multicomponent reaction between sulfonyl-protected imines, magnesium iodide, and acetylenic esters or ketones is described. The resulting β-iodo aza Morita-Baylis-Hillman adducts were obtained in good yields and excellent Z/E stereoselectivities. The reaction showed good tolerance for sulfonyl protecting groups, as well as for acetylenic ketones and esters. This work presents the first synthetic approach to β-iodo aza Morita-Baylis-Hillman adducts.
KW - Imines
KW - Magnesium iodide
KW - Morita-Baylis-Hillman adducts
KW - Multicomponent reactions
UR - http://www.scopus.com/inward/record.url?scp=33745009815&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2006.01.114
DO - 10.1016/j.tet.2006.01.114
M3 - Article
AN - SCOPUS:33745009815
SN - 0040-4020
VL - 62
SP - 7151
EP - 7154
JO - Tetrahedron
JF - Tetrahedron
IS - 30
ER -