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DOI: 10.1055/sos-SD-036-00701

Bingham, M. J.; Greaney, M. F.Science of Synthesis, (200836992.

The hydrolytic ring opening of aziridines 37 can be achieved under a range of conditions to afford β-amino alcohols with both stereo- and regiocontrol (e.g., conversion of 38 into 39, Scheme 17).[‌121‌,‌122‌] The regio- and stereoselectivities are determined by the nature of the protecting group on the nitrogen atom, the stereochemistry of the aziridine starting material, and the presence of neighboring functionality.

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8. Me8M (8.8 eeeee), Me8M (8 eeeee), MMMM (eee.), MM8Me8, 88°M, 88eee
8. MM8MMe8 (8 eeeee), MMM, 88°M, 8.8e
8. M8M, ee, 8e
88 [‌888‌]
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MeMM (8 eeeee), MeMM/M8M (8:8), ee 88 [‌888‌]
8. MM8MMe8 (8 eeeee), MeMM, eeeeee, 8e
8. ee MeMMM8
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MeMM, M8M 88 [‌888‌]
8. MM (8 eeeee), MMM, 8°M, 8e
8. Me8Me(MM)Me8 (8 eeeee)
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Me8MMMM8 (8.8 eeeee), M8M, 88°M 88 [‌888‌]
MMM (8.8 eeeee), M8M/MeMM (8:88) 88 [‌888‌]

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(8M,8M)-8-Meeee-8-eeeeeeeee-8-ee-8-ee (88); Meeeeee Meeeeeeee:[‌888‌]

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