Research output: Contribution to Journal/Magazine › Journal article › peer-review
Research output: Contribution to Journal/Magazine › Journal article › peer-review
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TY - JOUR
T1 - Unexpected products from the attempted organolithium-mediated conversion of beta-methoxy aziridines into allylic amines
AU - Coote, Susannah C.
AU - O'Brien, Peter
PY - 2010/1/27
Y1 - 2010/1/27
N2 - The organolithium-mediated conversion of cyclic trans-p-methoxy aziridines and cis-beta-methoxy aziridines with a tertiary alkoxy group adjacent to the aziridine into the corresponding substituted allylic sulfonamides is reported. In all cases, unexpected products were observed and the reactivity was completely different from other related cis-beta-methoxy aziridines. The product distributions are highly dependent on the organolithium reagent employed and the structure of the methoxy aziridine Thus, together with our previous reports, the full scope and limitations of this approach to allylic sulfonamides are established.
AB - The organolithium-mediated conversion of cyclic trans-p-methoxy aziridines and cis-beta-methoxy aziridines with a tertiary alkoxy group adjacent to the aziridine into the corresponding substituted allylic sulfonamides is reported. In all cases, unexpected products were observed and the reactivity was completely different from other related cis-beta-methoxy aziridines. The product distributions are highly dependent on the organolithium reagent employed and the structure of the methoxy aziridine Thus, together with our previous reports, the full scope and limitations of this approach to allylic sulfonamides are established.
KW - ALPHA-LITHIATION-REARRANGEMENT
KW - ALKOXY AZIRIDINES
KW - REDUCTIVE ALKYLATION
KW - SULFONAMIDES
KW - EPOXIDES
KW - ALCOHOLS
KW - ROUTE
U2 - 10.1016/j.tetlet.2009.11.059
DO - 10.1016/j.tetlet.2009.11.059
M3 - Journal article
VL - 51
SP - 588
EP - 590
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 4
ER -