Table 2. 1,5-HAT–S–T Sequence in 3-C-(α,β-d-Manp)1-propoxyphthalimides 5–8^a.

^aReagents and conditions: method A: n-Bu₃SnH (1 equiv), AIBN (0.1 equiv), PhCH₃ (0.013 M), reflux; method B: n-Bu₃SnH (1 equiv/h), AIBN (0.1 equiv), PhCH₃ (0.013 M), reflux; method C: TTMSS (1 equiv), AIBN (0.1 equiv), PhCH₃ (0.013 M), reflux; method D: n-Bu₃SnD (1 equiv), AIBN (0.1 equiv), PhCH₃ (0.013 M), reflux; method E: n-Bu₃SnD (1 equiv), BF₃•Et₂O (0.2 equiv), AIBN (0.1 equiv), PhCH₃ (0.013 M), reflux; method F: Hantzsch ester (1.1 equiv), fac-Ir(ppy)₃ (0.01 equiv), THF (0.007 M), rt, blue LED; and method G: Hantzsch ester (0.37 equiv/h), fac-Ir(ppy)₃ (0.01 equiv), THF (0.007 M), rt, blue LED.

^bValues in parentheses are isolate yields; deuterium incorporation (²H/¹H) is included in partially labeled compounds.