Trialkylamine versus trialkylphosphine: Catalytic conjugate addition of alcohols to alkyl propiolates

Synlett

Volumn , Issue 8, 2009, Pages 1223-1226

  Tejedor, David ^a,b   Santos Expósito, Alicia ^a,b   Méndez Abt, Gabriela ^a,b   Ruiz Pérez, Catalina ^c   García Tellado, Fernando ^a,b  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

^b Madrid Spain   (Spain)

^c UNIVERSIDAD DE LA LAGUNA   (Spain)

Author keywords

Alkynes; Amines; Bicyclic compounds; Catalysis; Phosphorus

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALCOHOL; ALKYNE DERIVATIVE; AMINE; BETA ALKOXYACRYLATE DERIVATIVE; BICYCLIC HEXAHYDROFURO[2,3 B]FURAN DERIVATIVE; FURAN DERIVATIVE; ORGANOTIN COMPOUND; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONJUGATE; OBSERVATION; SYNTHESIS;

EID: 67649304700     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1216727     Document Type: Article

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21. 2 proved to be the best catalytic system.
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24. This is true as long as the R1 substituent shown in Scheme 1 is an aliphatic group. It has been shown that activated propargylic alcohols bearing aromatic substituents isomerize to the corresponding alkenoates in the presence of tertiary amines: Sonye, J. P.; Koide, K. Org. Lett. 2006, 8, 199; and references cited therein.
25. Unactivated propargylic alcohols behave as expected affording the corresponding product 1 (see ref. 1).
26. +], 295 (61), 294 (100), 166 (69), 163 (55), 77 (49), 59 (38), 51 (35).