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Pyrrole‐Protected β‐Aminoalkylzinc Reagents for the Enantioselective Synthesis of Amino‐Derivatives
Author(s) -
Leroux Marcel,
Huang WanYun,
Lemke Yannick,
Koller Thaddäus J.,
Karaghiosoff Konstantin,
Knochel Paul
Publication year - 2020
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202000870
Subject(s) - chemistry , enantioselective synthesis , pyrrole , negishi coupling , reagent , amino acid , organic chemistry , acylation , zinc , halide , alkyl , catalysis , biochemistry
Chiral β‐aminoalkylzinc halides were prepared starting from optically pure commercial β‐amino‐alcohols. These amino‐alcohols were converted to the corresponding N ‐pyrrolyl‐protected alkyl iodides which undergo a zinc insertion in the presence of LiCl (THF, 25 °C, 10–90 min). Subsequent Negishi cross‐coupling or acylation reactions with acid chlorides produced amino‐derivatives with retention of chirality. Diastereoselective CBS‐reductions of some prepared N ‐pyrrolyl‐ketones provided 1,3‐subsituted N ‐pyrrolyl‐alcohols with high diastereoselectivity. Additionally, a deprotection procedure involving an ozonolysis allowed the conversion of the pyrrole‐ring into a formamide without loss of optical purity.