Journal
ACS CATALYSIS
Volume 12, Issue 20, Pages 12530-12542Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.2c03909
Keywords
hexafluoroisopropanol (HFIP); late-stage functionalization; high-throughput screening; cyclopropanation; rhodium carbene
Categories
Funding
- NIBR
- National Science Foundation [CHE 1531620, CHE 1626172, CHE-1700982, CHE-1956154]
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In the presence of HFIP, nucleophilic and reactive reagents are prevented from interacting with a rhodium carbene, allowing for efficient asymmetric cyclopropanation with high yield and stereoselectivity on a variety of compounds. A high-throughput screen was conducted to expand the scope of the reaction and develop complementary catalytic systems, leading to the enantioselective functionalization of complex molecules including API and natural products.
In the presence of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP), nucleophilic and reactive reagents are prevented from interacting with a rhodium carbene, allowing asymmetric cyclopropanation to occur with high yield and stereoselectivity on a variety of compounds. A high-throughput screen was conducted on cyclopropanation with a complementary catalytic system in the presence of 90 different poisonous nucleophiles and varying amounts of HFIP (10 equiv, used as reaction solvent). The scope of both the aryl/heteroaryl diazoacetate and the olefin was expanded, and the study culminated in the enantioselective functionalization of complex molecules including API and natural products.
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