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Lewis base catalyzed enantioselective aldol addition of acetaldehyde-derived silyl enol ether to aldehydes.
J Org Chem. 2005 Nov 25; 70(24):10190-3.JO

Abstract

[reaction: see text] Chiral phosphoramide catalyzed-enantioselective aldol addition of an acetaldehyde-derived trialkylsilyl enol ether to aromatic aldehydes provides protected aldol products in good yields with good to excellent enantioselectivities. Preliminary studies show that the aldolization intermediate (a chlorohydrin adduct) can be trapped with tert-butyl isocyanide to form an alpha-hydroxy lactone with good selectivity in a single-pot operation.

Authors+Show Affiliations

Roger Adams Laboratory, Department of Chemistry, 600 South Mathews Avenue, University of Illinois, Urbana, Illinois 61801, USA. denmark@scs.uiuc.eduNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

16292871

Citation

Denmark, Scott E., and Tommy Bui. "Lewis Base Catalyzed Enantioselective Aldol Addition of Acetaldehyde-derived Silyl Enol Ether to Aldehydes." The Journal of Organic Chemistry, vol. 70, no. 24, 2005, pp. 10190-3.
Denmark SE, Bui T. Lewis base catalyzed enantioselective aldol addition of acetaldehyde-derived silyl enol ether to aldehydes. J Org Chem. 2005;70(24):10190-3.
Denmark, S. E., & Bui, T. (2005). Lewis base catalyzed enantioselective aldol addition of acetaldehyde-derived silyl enol ether to aldehydes. The Journal of Organic Chemistry, 70(24), 10190-3.
Denmark SE, Bui T. Lewis Base Catalyzed Enantioselective Aldol Addition of Acetaldehyde-derived Silyl Enol Ether to Aldehydes. J Org Chem. 2005 Nov 25;70(24):10190-3. PubMed PMID: 16292871.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Lewis base catalyzed enantioselective aldol addition of acetaldehyde-derived silyl enol ether to aldehydes. AU - Denmark,Scott E, AU - Bui,Tommy, PY - 2005/11/19/pubmed PY - 2005/11/19/medline PY - 2005/11/19/entrez SP - 10190 EP - 3 JF - The Journal of organic chemistry JO - J Org Chem VL - 70 IS - 24 N2 - [reaction: see text] Chiral phosphoramide catalyzed-enantioselective aldol addition of an acetaldehyde-derived trialkylsilyl enol ether to aromatic aldehydes provides protected aldol products in good yields with good to excellent enantioselectivities. Preliminary studies show that the aldolization intermediate (a chlorohydrin adduct) can be trapped with tert-butyl isocyanide to form an alpha-hydroxy lactone with good selectivity in a single-pot operation. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/16292871/Lewis_base_catalyzed_enantioselective_aldol_addition_of_acetaldehyde_derived_silyl_enol_ether_to_aldehydes_ DB - PRIME DP - Unbound Medicine ER -
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