Highly enantioselective synthesis of γ-, δ-, and ε-chiral 1-alkanols via Zr-catalyzed asymmetric carboalumination of alkenes (ZACA)–Cu- or Pd-catalyzed cross-coupling

Significance Chirality plays a vital role in chemical, biological, pharmaceutical, and material sciences. The preparation of enantiomerically pure compounds is a very important and challenging area. In this paper, we developed a highly enantioselective (≥99%ee ) and widely applicable method for the synthesis of various γ- and more-remotely chiral alcohols, many of which cannot be satisfactorily prepared by other existing methods, via the ZACA/oxidation–lipase-catalyzed acetylation–Cu- or Pd-catalyzed cross-coupling from terminal alkenes. We also demonstrated MαNP ester analysis is a convenient and powerful method for determining the enantiomeric purities of δ- and ε-chiral primary alkanols. This finding is anticipated to shed light on the relatively undeveloped field of determination of enantiomeric purity and/or absolute configuration of remotely chiral primary alcohols.