Iridium-Catalyzed Enantioselective Synthesis of α-Chiral Bicyclo[1.1.1]pentanes by 1,3-Difunctionalization of [1.1.1]Propellane.
2020
Bicyclo[1.1.1]pentanes
(BCPs) have found application as bioisosteres
of aromatic rings in drug development. However, catalytic construction
of this motif with adjacent stereocenters with high enantioselectivity
from readily available starting materials still constitutes a significant
synthetic challenge. Herein we report a direct stereoselective synthesis
of α-chiral allylic BCPs by 1,3-difunctionalization of [1.1.1]propellane
with Grignard reagents and allyl carbonates using iridium catalysis.
This mild protocol proceeds via initial organometallic addition to
[1.1.1]propellane followed by asymmetric allylic substitution, providing
the products with high enantioselectivities over a broad range of
substrates. Further derivatization of the products demonstrates the
applicability of this method to the preparation of structurally diverse
libraries of chiral BCP derivatives.
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