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Water-compatible organocatalysts for direct asymmetric syn-aldol reactions of dihydroxyacetone and aldehydes.
Org Lett. 2008 Apr 17; 10(8):1621-4.OL

Abstract

A novel organocatalyst was developed that effectively catalyzed the reactions of unprotected or protected dihydroxyacetone with a variety of aldehydes to provide syn-aldol products with good yields and ee values up to >99%. Significantly, this amide catalyst was effective with a variety of nonaromatic aldehyde acceptors that had proven difficult in the presence of other catalysts. Reactions of protected dihydroxyacetone proceeded in aqueous media without addition of organic solvents.

Authors+Show Affiliations

The Skaggs Institute for Chemical Biology, and Departments of Chemistry and Molecular Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.No affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18351769

Citation

Ramasastry, S S V., et al. "Water-compatible Organocatalysts for Direct Asymmetric Syn-aldol Reactions of Dihydroxyacetone and Aldehydes." Organic Letters, vol. 10, no. 8, 2008, pp. 1621-4.
Ramasastry SS, Albertshofer K, Utsumi N, et al. Water-compatible organocatalysts for direct asymmetric syn-aldol reactions of dihydroxyacetone and aldehydes. Org Lett. 2008;10(8):1621-4.
Ramasastry, S. S., Albertshofer, K., Utsumi, N., & Barbas, C. F. (2008). Water-compatible organocatalysts for direct asymmetric syn-aldol reactions of dihydroxyacetone and aldehydes. Organic Letters, 10(8), 1621-4. https://doi.org/10.1021/ol8002833
Ramasastry SS, et al. Water-compatible Organocatalysts for Direct Asymmetric Syn-aldol Reactions of Dihydroxyacetone and Aldehydes. Org Lett. 2008 Apr 17;10(8):1621-4. PubMed PMID: 18351769.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Water-compatible organocatalysts for direct asymmetric syn-aldol reactions of dihydroxyacetone and aldehydes. AU - Ramasastry,S S V, AU - Albertshofer,Klaus, AU - Utsumi,Naoto, AU - Barbas,Carlos F,3rd Y1 - 2008/03/20/ PY - 2008/3/21/pubmed PY - 2008/6/3/medline PY - 2008/3/21/entrez SP - 1621 EP - 4 JF - Organic letters JO - Org Lett VL - 10 IS - 8 N2 - A novel organocatalyst was developed that effectively catalyzed the reactions of unprotected or protected dihydroxyacetone with a variety of aldehydes to provide syn-aldol products with good yields and ee values up to >99%. Significantly, this amide catalyst was effective with a variety of nonaromatic aldehyde acceptors that had proven difficult in the presence of other catalysts. Reactions of protected dihydroxyacetone proceeded in aqueous media without addition of organic solvents. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/18351769/Water_compatible_organocatalysts_for_direct_asymmetric_syn_aldol_reactions_of_dihydroxyacetone_and_aldehydes_ DB - PRIME DP - Unbound Medicine ER -