Scope of oxazoline coupling (only single diastereoisomer of product shown).
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Conditions A: 6 (1.1 eq), Pd(OAc)2 (5 mol%), (t-Bu)2P(O)H (10 mol%), LiOt-Bu (2.5 eq); conditions B: 6 (2.2 eq), Pd(OAc)2 (10 mol%), (t-Bu)2P(O)H (20 mol%), LiOt-Bu (5.0 eq); conditions C: 6 (4.4 eq), Pd(OAc)2 (40 mol%), (t-Bu)2P(O)H (80 mol%), LiOt-Bu (10.0 eq); conditions D: 6 (1.1 eq), Pd(OAc)2 (5 mol%), (Ad)2P(O)H (10 mol%), LiOt-Bu (2.5 eq); conditions E: 6 (4.4 eq), Pd(OAc)2 (40 mol%), (Ad)2P(O)H (80 mol%), LiOt-Bu (10.0 eq); conditions F: 6 (2.2 eq), Pd(OAc)2 (10 mol%), (Ad)2P(O)H (20 mol%), LiOt-Bu (5.0 eq).
Only single diastereoisomer shown in table. Diastereoisomers in red cannot be separated. Diastereoisomers in blue are partially resolved.
Yield of separate diastereomers (diastereomer1)%/(diastereomer2)%.
Combined yield of all stereoisomers (includes mixed fractions).