TY - DATA T1 - Organo-Manganese η2‑Auxiliary Directed Reactions: A Diastereoselective Approach to 2,3-Allenols PY - 2015/02/20 AU - Animesh Roy AU - Bilal A. Bhat AU - Salvatore D. Lepore UR - https://acs.figshare.com/articles/journal_contribution/Organo_Manganese_sup_2_sup_Auxiliary_Directed_Reactions_A_Diastereoselective_Approach_to_2_3_Allenols/2194219 DO - 10.1021/ol503757h.s001 L4 - https://ndownloader.figshare.com/files/3828544 KW - methylcyclopentadienyl manganese tricarbonyl KW - diastereoselective additions KW - aldehyde carbonyl KW - Diastereoselective Approach KW - MMT KW - allenyl aldehydes KW - allenol KW - allene moiety N2 - Propargyl aldehydes underwent isomerization to allenyl aldehydes under mildly basic conditions when complexed to an organo-manganese auxiliary using methylcyclopentadienyl manganese tricarbonyl (MMT). This traceless auxiliary magnifies the axial chirality of the allene moiety, allowing for highly diastereoselective additions to the aldehyde carbonyl and subsequent access to an array of 2,3-allenols. Using this strategy, a nitrile-substituted 2,3-allenol was prepared and efficiently converted to Hagen’s gland lactone. ER -