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Stereoselective vinylogous Mukaiyama aldol reaction of α-haloenals.
Chem Pharm Bull (Tokyo). 2011; 59(4):522-4.CP

Abstract

We have developed a high-yielding and stereoselective vinylogous Mukaiyama aldol reaction (VMAR) of α-haloenals. Contrary to the simple α,β-unsaturated aldehyde, α-haloenals were found to be reactive affording the corresponding VMAR adducts in excellent yields. Some transformations of VMAR adducts by Pd-mediated cross-coupling were also examined in order to demonstrate the synthetic utility of VMAR of α-haloenals.

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Authors+Show Affiliations

Iwasaki Y
Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, Japan.
Matsui R
No affiliation info available
Suzuki T
No affiliation info available
Nakazaki A
No affiliation info available
Kobayashi S
No affiliation info available

MeSH

AldehydesCatalysisPalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21467689

Citation

Iwasaki, Yoichi, et al. "Stereoselective Vinylogous Mukaiyama Aldol Reaction of Α-haloenals." Chemical & Pharmaceutical Bulletin, vol. 59, no. 4, 2011, pp. 522-4.
Iwasaki Y, Matsui R, Suzuki T, et al. Stereoselective vinylogous Mukaiyama aldol reaction of α-haloenals. Chem Pharm Bull (Tokyo). 2011;59(4):522-4.
Iwasaki, Y., Matsui, R., Suzuki, T., Nakazaki, A., & Kobayashi, S. (2011). Stereoselective vinylogous Mukaiyama aldol reaction of α-haloenals. Chemical & Pharmaceutical Bulletin, 59(4), 522-4.
Iwasaki Y, et al. Stereoselective Vinylogous Mukaiyama Aldol Reaction of Α-haloenals. Chem Pharm Bull (Tokyo). 2011;59(4):522-4. PubMed PMID: 21467689.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective vinylogous Mukaiyama aldol reaction of α-haloenals. AU - Iwasaki,Yoichi, AU - Matsui,Ryosuke, AU - Suzuki,Takahiro, AU - Nakazaki,Atsuo, AU - Kobayashi,Susumu, PY - 2011/4/7/entrez PY - 2011/4/7/pubmed PY - 2011/7/20/medline SP - 522 EP - 4 JF - Chemical & pharmaceutical bulletin JO - Chem Pharm Bull (Tokyo) VL - 59 IS - 4 N2 - We have developed a high-yielding and stereoselective vinylogous Mukaiyama aldol reaction (VMAR) of α-haloenals. Contrary to the simple α,β-unsaturated aldehyde, α-haloenals were found to be reactive affording the corresponding VMAR adducts in excellent yields. Some transformations of VMAR adducts by Pd-mediated cross-coupling were also examined in order to demonstrate the synthetic utility of VMAR of α-haloenals. SN - 1347-5223 UR - https://www.unboundmedicine.com/medline/citation/21467689/Stereoselective_vinylogous_Mukaiyama_aldol_reaction_of_α_haloenals_ L2 - https://joi.jlc.jst.go.jp/JST.JSTAGE/cpb/59.522?from=PubMed DB - PRIME DP - Unbound Medicine ER -