γ-Substituted Allenic Amides in the Phosphine-Catalyzed Enantioselective Higher Order Cycloaddition with Azaheptafulvenes

Racemic γ-substituted allenes undergo enantioselective higher order [8 + 2]-cycloaddition with azaheptafulvenes using a chiral amino acid derived amidophosphine as catalyst, providing the corresponding azaazulenoid cycloadducts with excellent levels of regio-, diastereo-, and enantioselectivities. I...

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Bibliographic Details
Published in:	Organic letters Vol. 22; no. 12; pp. 4721 - 4725
Main Authors:	Manzano, Rubén, Romaniega, Aketza, Prieto, Liher, Díaz, Estíbaliz, Reyes, Efraim, Uria, Uxue, Carrillo, Luisa, Vicario, Jose L
Format:	Journal Article
Language:	English
Published:	United States 19-06-2020
Online Access:	Get full text
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Summary:	Racemic γ-substituted allenes undergo enantioselective higher order [8 + 2]-cycloaddition with azaheptafulvenes using a chiral amino acid derived amidophosphine as catalyst, providing the corresponding azaazulenoid cycloadducts with excellent levels of regio-, diastereo-, and enantioselectivities. In this reaction, the activated allylic phosphonium ylide intermediate participates as the C -component of the reaction, in contrast to the conventional reactivity of this type of zwitterionic intermediates as C -components in cycloaddition reactions.
Bibliography:	ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1523-7060 1523-7052
DOI:	10.1021/acs.orglett.0c01523