Journal
HETEROCYCLES
Volume 80, Issue 2, Pages 887-893Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-09-S(S)116
Keywords
Enantioselective 1,3-Dipolar Cycloaddition; Azomethine Imine; Optically Active Pyrazolidine; Magnesium Bromide; Diisopropyl (R,R)-Tartrate
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Funding
- Ministry of Education, Culture, Sports, Science and Technology (MEXT)
- Japan Society for the Promotion of Science (JSPS)
- Grants-in-Aid for Scientific Research [21550038] Funding Source: KAKEN
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The catalytic regio- and enantioselective 1,3-dipolar cycloaddition of azomethine imines to allyl alcohol was achieved by utilizing diisopropyl (R,R)-tartrate as a chiral auxiliary to afford the corresponding optically active trans-pyrazolidines with enantioselectivities up to 93% ee. Addition of MgBr2 was crucial to realize reproducible high enantioselectivity.
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