Journal
ORGANIC LETTERS
Volume 18, Issue 11, Pages 2620-2623Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.6b01047
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Funding
- NIH [GM105766, F31 GM111050]
- NSERC (PGS-D3 fellowship)
- Eli Lilly
- Novartis
- Bristol-Myers Squibb
- Amgen
- Boehringer-Ingelheim
- Sloan Foundation
- Baxter Foundation
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Hydrogen atom transfer (HAT) circumvents a disfavored Friedel-Crafts reaction in the derivatization of the inexpensive monoterpene isopulegol. A variety of readily prepared aryl and heteroaryl sulfonates undergo a formal hydroarylation to form 8-arylmenthols, privileged scaffolds for asymmetric synthesis, as typified by 8-phenylmenthol. High stereoselectivity is observed in related systems. This use of HAT significantly extends the chiral pool from the inexpensive monoterpene isopulegol.
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