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Rhodium-catalyzed intramolecular hydroacylation of 5- and 6-alkynals: convenient synthesis of alpha-alkylidenecycloalkanones and cycloalkenones.
Chemistry. 2004 Nov 05; 10(22):5681-8.C

Abstract

A novel intramolecular hydroacylation of 5- and 6-alkynals leading to alpha-alkylidenecycloalkanones was accomplished by using cationic a rhodium(I)/BINAP complex. For all cyclizations described, a single (E)-olefin isomer was obtained. At elevated temperature, hydroacylation and double bond migration of 5- and 6-alkynals proceeded in a one-pot reaction to give cycloalkenones. An intramolecular hydroacylation of a 7-alkynal was unsuccessful. This method represents an attractive new route to highly functionalized alpha-alkylidenecycloalkanones and cycloalkenones.

Authors+Show Affiliations

Takeishi K
Department of Applied Chemistry, Graduate School of Engineering, Tokyo University of Agriculture and Technology, Koganei, Tokyo 184-8588, Japan.
Sugishima K
No affiliation info available
Sasaki K
No affiliation info available
Tanaka K
No affiliation info available

MeSH

AcylationAldehydesAlkanesAlkylationCatalysisCationsCyclizationHydroxylationMolecular StructureRhodium

Pub Type(s)

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

Language

eng

PubMed ID

15470696

Citation

Takeishi, Kenzo, et al. "Rhodium-catalyzed Intramolecular Hydroacylation of 5- and 6-alkynals: Convenient Synthesis of Alpha-alkylidenecycloalkanones and Cycloalkenones." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 10, no. 22, 2004, pp. 5681-8.
Takeishi K, Sugishima K, Sasaki K, et al. Rhodium-catalyzed intramolecular hydroacylation of 5- and 6-alkynals: convenient synthesis of alpha-alkylidenecycloalkanones and cycloalkenones. Chemistry. 2004;10(22):5681-8.
Takeishi, K., Sugishima, K., Sasaki, K., & Tanaka, K. (2004). Rhodium-catalyzed intramolecular hydroacylation of 5- and 6-alkynals: convenient synthesis of alpha-alkylidenecycloalkanones and cycloalkenones. Chemistry (Weinheim an Der Bergstrasse, Germany), 10(22), 5681-8.
Takeishi K, et al. Rhodium-catalyzed Intramolecular Hydroacylation of 5- and 6-alkynals: Convenient Synthesis of Alpha-alkylidenecycloalkanones and Cycloalkenones. Chemistry. 2004 Nov 5;10(22):5681-8. PubMed PMID: 15470696.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rhodium-catalyzed intramolecular hydroacylation of 5- and 6-alkynals: convenient synthesis of alpha-alkylidenecycloalkanones and cycloalkenones. AU - Takeishi,Kenzo, AU - Sugishima,Koudai, AU - Sasaki,Kaori, AU - Tanaka,Ken, PY - 2004/10/8/pubmed PY - 2006/5/18/medline PY - 2004/10/8/entrez SP - 5681 EP - 8 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 10 IS - 22 N2 - A novel intramolecular hydroacylation of 5- and 6-alkynals leading to alpha-alkylidenecycloalkanones was accomplished by using cationic a rhodium(I)/BINAP complex. For all cyclizations described, a single (E)-olefin isomer was obtained. At elevated temperature, hydroacylation and double bond migration of 5- and 6-alkynals proceeded in a one-pot reaction to give cycloalkenones. An intramolecular hydroacylation of a 7-alkynal was unsuccessful. This method represents an attractive new route to highly functionalized alpha-alkylidenecycloalkanones and cycloalkenones. SN - 0947-6539 UR - https://www.unboundmedicine.com/medline/citation/15470696/Rhodium_catalyzed_intramolecular_hydroacylation_of_5__and_6_alkynals:_convenient_synthesis_of_alpha_alkylidenecycloalkanones_and_cycloalkenones_ DB - PRIME DP - Unbound Medicine ER -