Catalytic asymmetric transacetalization.

A catalytic enantioselective transacetalization has been developed. The chiral phosphoric acid TRIP was demonstrated to be an efficient and highly enantioselective catalyst for the activation of O,O-acetals. The reaction enables the asymmetric synthesis of acetals with the acetal carbon as the only stereogenic center.

• Publication year

  2010

• Venue

  Journal of the American Chemical Society

• Publication date

  2010-06-07

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1021/ja102753dPMID 20527773
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• The reaction enables asymmetric synthesis of acetals in which the acetal carbon is the only stereogenic center.

  Confidence 0.95

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewKiller Whale (322360f1c1) reviewAK (4715169a40) review
• Chiral phosphoric acid TRIP efficiently catalyzes an enantioselective transacetalization of O,O-acetals.

  Confidence 0.97

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewKiller Whale (322360f1c1) reviewAK (4715169a40) review

• acetal carbon

  atom

  The carbon atom in an acetal framework that becomes the stereogenic carbon in the products.

  Aliases: anomeric carbon

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewKiller Whale (322360f1c1) reviewAK (4715169a40) review
• acetals

  compound class

  The acetal products formed by transacetalization in this reaction.

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewKiller Whale (322360f1c1) reviewAK (4715169a40) review
• asymmetric synthesis

  synthetic strategy

  A synthetic approach that produces chiral products in an enantioselective form.

  Aliases: asymmetric synthesis of acetals

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewKiller Whale (322360f1c1) reviewAK (4715169a40) review
• catalytic enantioselective transacetalization

  reaction

  A catalyst-driven acetal exchange reaction that is conducted in an enantioselective manner.

  Aliases: enantioselective transacetalization

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewKiller Whale (322360f1c1) reviewAK (4715169a40) review
• chiral phosphoric acid trip

  catalyst

  A chiral phosphoric acid catalyst used to promote the transacetalization in this work.

  Aliases: TRIP

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewKiller Whale (322360f1c1) reviewAK (4715169a40) review
• o,o-acetals

  substrate

  Acetal substrates containing two oxygen substituents at the acetal carbon that are activated in the reaction.

  Aliases: O,O-acetal

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewKiller Whale (322360f1c1) reviewAK (4715169a40) review
• stereogenic center

  structural feature

  An atom in a molecule whose distinct substituents give rise to chirality.

  Aliases: chiral center

  박진우 (dztg5apj7m) extractionB (s683577b42) reviewKiller Whale (322360f1c1) reviewAK (4715169a40) review

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