Cover Image

Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives

An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals has been developed for the synthesis of indenone derivatives. A wide variety of functionalized indenone derivatives can be obtained in good-to-excellent yields. HMBC and NOESY NMR analyses and mechanistic elucidation experim...

Full description

Saved in:
Bibliographic Details
Main Authors: Yamada, Tsuyoshi (Author) , Park, Kwihwan (Author) , Tachikawa, Takumu (Author) , Fujii, Akiko (Author) , Rudolph, Matthias (Author) , Hashmi, A. Stephen K. (Author) , Sajiki, Hironao (Author)
Format: Article (Journal)
Language:English
Published: [2020]
In: Organic letters
Year: 2020, Volume: 22, Issue: 5, Pages: 1883-1888
ISSN:1523-7052
DOI:10.1021/acs.orglett.0c00221
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.orglett.0c00221
Get full text
Author Notes:Tsuyoshi Yamada, Kwihwan Park, Takumu Tachikawa, Akiko Fujii, Matthias Rudolph, A. Stephen K. Hashmi, and Hironao Sajiki

MARC

LEADER 00000caa a2200000 c 4500
001 1694948293
003 DE-627
005 20230427070547.0
007 cr uuu---uuuuu
008 200420s2020 xx |||||o 00| ||eng c
024 7 |a 10.1021/acs.orglett.0c00221  |2 doi 
035 |a (DE-627)1694948293 
035 |a (DE-599)KXP1694948293 
035 |a (OCoLC)1341315625 
040 |a DE-627  |b ger  |c DE-627  |e rda 
041 |a eng 
084 |a 30  |2 sdnb 
100 1 |a Yamada, Tsuyoshi  |e VerfasserIn  |0 (DE-588)1208638890  |0 (DE-627)1694948609  |4 aut 
245 1 0 |a Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives  |c Tsuyoshi Yamada, Kwihwan Park, Takumu Tachikawa, Akiko Fujii, Matthias Rudolph, A. Stephen K. Hashmi, and Hironao Sajiki 
264 1 |c [2020] 
300 |b Illustrationen 
300 |a 6 
336 |a Text  |b txt  |2 rdacontent 
337 |a Computermedien  |b c  |2 rdamedia 
338 |a Online-Ressource  |b cr  |2 rdacarrier 
500 |a Gesehen am 20.04.2020 
520 |a An efficient gold-catalyzed cyclization of 2-alkynylaldehyde cyclic acetals has been developed for the synthesis of indenone derivatives. A wide variety of functionalized indenone derivatives can be obtained in good-to-excellent yields. HMBC and NOESY NMR analyses and mechanistic elucidation experiments revealed that the cyclization occurs via a 1,5-H shift. The cyclic acetal group promoted the 1,5-H shift by activating the benzylic C-H bond and preventing the migration of the alkoxy group by tethering both alkoxy groups. 
700 1 |a Park, Kwihwan  |e VerfasserIn  |4 aut 
700 1 |a Tachikawa, Takumu  |e VerfasserIn  |4 aut 
700 1 |a Fujii, Akiko  |e VerfasserIn  |4 aut 
700 1 |a Rudolph, Matthias  |d 1975-  |e VerfasserIn  |0 (DE-588)136790380  |0 (DE-627)587252405  |0 (DE-576)301277524  |4 aut 
700 1 |a Hashmi, A. Stephen K.  |d 1963-  |e VerfasserIn  |0 (DE-588)101199576X  |0 (DE-627)704823926  |0 (DE-576)169176665  |4 aut 
700 1 |a Sajiki, Hironao  |e VerfasserIn  |4 aut 
773 0 8 |i Enthalten in  |t Organic letters  |d Washington, DC : ACS, 1999  |g 22(2020), 5, Seite 1883-1888  |h Online-Ressource  |w (DE-627)306717662  |w (DE-600)1501522-1  |w (DE-576)082438013  |x 1523-7052  |7 nnas  |a Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives 
773 1 8 |g volume:22  |g year:2020  |g number:5  |g pages:1883-1888  |g extent:6  |a Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives 
856 4 0 |u https://doi.org/10.1021/acs.orglett.0c00221  |x Verlag  |x Resolving-System  |z lizenzpflichtig  |3 Volltext 
951 |a AR 
992 |a 20200420 
993 |a Article 
994 |a 2020 
998 |g 101199576X  |a Hashmi, A. Stephen K.  |m 101199576X:Hashmi, A. Stephen K.  |d 120000  |d 120100  |e 120000PH101199576X  |e 120100PH101199576X  |k 0/120000/  |k 1/120000/120100/  |p 6 
998 |g 136790380  |a Rudolph, Matthias  |m 136790380:Rudolph, Matthias  |d 120000  |d 120100  |e 120000PR136790380  |e 120100PR136790380  |k 0/120000/  |k 1/120000/120100/  |p 5 
999 |a KXP-PPN1694948293  |e 3626964078 
BIB |a Y 
SER |a journal 
JSO |a {"origin":[{"dateIssuedDisp":"[2020]","dateIssuedKey":"2020"}],"recId":"1694948293","language":["eng"],"note":["Gesehen am 20.04.2020"],"name":{"displayForm":["Tsuyoshi Yamada, Kwihwan Park, Takumu Tachikawa, Akiko Fujii, Matthias Rudolph, A. Stephen K. Hashmi, and Hironao Sajiki"]},"physDesc":[{"extent":"6 S.","noteIll":"Illustrationen"}],"relHost":[{"part":{"extent":"6","year":"2020","volume":"22","text":"22(2020), 5, Seite 1883-1888","pages":"1883-1888","issue":"5"},"disp":"Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone DerivativesOrganic letters","type":{"media":"Online-Ressource","bibl":"periodical"},"title":[{"title":"Organic letters","title_sort":"Organic letters"}],"physDesc":[{"extent":"Online-Ressource"}],"id":{"issn":["1523-7052"],"eki":["306717662"],"zdb":["1501522-1"]},"origin":[{"dateIssuedKey":"1999","dateIssuedDisp":"1999-","publisher":"ACS","publisherPlace":"Washington, DC"}],"recId":"306717662","language":["eng"],"note":["Gesehen am 25.08.2020"],"name":{"displayForm":["American Chemical Society"]},"pubHistory":["1.1999 -"]}],"title":[{"title":"Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives","title_sort":"Gold-Catalyzed Cyclization of 2-Alkynylaldehyde Cyclic Acetals via Hydride Shift for the Synthesis of Indenone Derivatives"}],"type":{"media":"Online-Ressource","bibl":"article-journal"},"id":{"eki":["1694948293"],"doi":["10.1021/acs.orglett.0c00221"]},"person":[{"given":"Tsuyoshi","role":"aut","display":"Yamada, Tsuyoshi","family":"Yamada"},{"given":"Kwihwan","role":"aut","display":"Park, Kwihwan","family":"Park"},{"family":"Tachikawa","display":"Tachikawa, Takumu","role":"aut","given":"Takumu"},{"family":"Fujii","display":"Fujii, Akiko","role":"aut","given":"Akiko"},{"family":"Rudolph","display":"Rudolph, Matthias","role":"aut","given":"Matthias"},{"role":"aut","given":"A. Stephen K.","family":"Hashmi","display":"Hashmi, A. Stephen K."},{"role":"aut","given":"Hironao","family":"Sajiki","display":"Sajiki, Hironao"}]} 
SRT |a YAMADATSUYGOLDCATALY2020 

Similar Items