Journal
ORGANIC LETTERS
Volume 23, Issue 15, Pages 5896-5900Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01986
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Funding
- JSPS KAKENHI [JP20H04801, JP19H05630]
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A three-pot asymmetric synthesis method was developed to produce anti-1,3-diol unit through three sequential reactions, including enantioselective Aldol reaction, diastereoselective anti-epoxidation, and reductive opening of the epoxide, achieving excellent diastereo- and enantioselectivity.
A three-pot asymmetric synthesis of the anti-1,3-diol unit was developed. In the first pot, enantioselective aldol reaction of aldehydes proceeds, catalyzed by organocatalyst, followed by either Wittig or Horner-Wadsworth-Emmons reactions to afford delta-hydroxy alpha,beta-unsaturated carbonyls with excellent enantioselectivity. Diastereoselective hydroxy-directed anti-epoxidation proceeds in the next pot by the use of tert-BuOOH and LiHMDS. Reductive opening of the epoxide proceeds in a third pot to afford anti-beta,delta-hydroxy carbonyl compounds with excellent diastereo- and enantioselectivity.
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