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A switch of facial selectivities using alpha-heteroatom-substituted aldehydes in the vinylogous Mukaiyama aldol reaction.
Org Lett. 2009 Mar 19; 11(6):1277-80.OL

Abstract

The vinylogous Mukaiyama aldol reaction (VMAR) of chiral nonracemic ketene silyl N,O-acetal with various aldehydes is demonstrated. VMAR with alpha-heteroatom-unsubstituted aldehydes proceeded with a high degree of anti-selectivity. In sharp contrast, moderate to high syn-selectivity was observed when alpha-heteroatom-substituted aldehydes were used.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Shinoyama M
Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan.
Shirokawa S
No affiliation info available
Nakazaki A
No affiliation info available
Kobayashi S
No affiliation info available

MeSH

AldehydesAlkenesCombinatorial Chemistry TechniquesMolecular StructureOxazolesSilanesStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

19222172

Citation

Shinoyama, Mariko, et al. "A Switch of Facial Selectivities Using Alpha-heteroatom-substituted Aldehydes in the Vinylogous Mukaiyama Aldol Reaction." Organic Letters, vol. 11, no. 6, 2009, pp. 1277-80.
Shinoyama M, Shirokawa S, Nakazaki A, et al. A switch of facial selectivities using alpha-heteroatom-substituted aldehydes in the vinylogous Mukaiyama aldol reaction. Org Lett. 2009;11(6):1277-80.
Shinoyama, M., Shirokawa, S., Nakazaki, A., & Kobayashi, S. (2009). A switch of facial selectivities using alpha-heteroatom-substituted aldehydes in the vinylogous Mukaiyama aldol reaction. Organic Letters, 11(6), 1277-80. https://doi.org/10.1021/ol9000312
Shinoyama M, et al. A Switch of Facial Selectivities Using Alpha-heteroatom-substituted Aldehydes in the Vinylogous Mukaiyama Aldol Reaction. Org Lett. 2009 Mar 19;11(6):1277-80. PubMed PMID: 19222172.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A switch of facial selectivities using alpha-heteroatom-substituted aldehydes in the vinylogous Mukaiyama aldol reaction. AU - Shinoyama,Mariko, AU - Shirokawa,Shin-ichi, AU - Nakazaki,Atsuo, AU - Kobayashi,Susumu, PY - 2009/2/19/entrez PY - 2009/2/19/pubmed PY - 2009/4/10/medline SP - 1277 EP - 80 JF - Organic letters JO - Org Lett VL - 11 IS - 6 N2 - The vinylogous Mukaiyama aldol reaction (VMAR) of chiral nonracemic ketene silyl N,O-acetal with various aldehydes is demonstrated. VMAR with alpha-heteroatom-unsubstituted aldehydes proceeded with a high degree of anti-selectivity. In sharp contrast, moderate to high syn-selectivity was observed when alpha-heteroatom-substituted aldehydes were used. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/19222172/A_switch_of_facial_selectivities_using_alpha_heteroatom_substituted_aldehydes_in_the_vinylogous_Mukaiyama_aldol_reaction_ L2 - https://doi.org/10.1021/ol9000312 DB - PRIME DP - Unbound Medicine ER -