Diverse saturated heterocycles from a hydroacylation/conjugate addition cascade

Rhodium-catalyzed hydroacylation using alkynes substituted with pendant nucleophiles, delivers linear α,β-unsaturated enone intermediates with excellent regioselectivity. These adducts are used to construct a broad range of diversely substituted, saturated O-, N- and S-heterocycles in a one-pot proc...

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Bibliographic Details
Published in:	Chemical science (Cambridge) Vol. 13; no. 5; pp. 154 - 1511
Main Authors:	Iwumene, Ndidi U. N, Moseley, Daniel. F, Pullin, Robert D. C, Willis, Michael C
Format:	Journal Article
Language:	English
Published:	England Royal Society of Chemistry 02-02-2022 The Royal Society of Chemistry
Subjects:	Adducts Alkynes Catalysis Chemistry Nucleophiles Regioselectivity Rhodium Stereoselectivity Substitutes
Online Access:	Get full text
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Summary:	Rhodium-catalyzed hydroacylation using alkynes substituted with pendant nucleophiles, delivers linear α,β-unsaturated enone intermediates with excellent regioselectivity. These adducts are used to construct a broad range of diversely substituted, saturated O-, N- and S-heterocycles in a one-pot process. Judicious choice of cyclisation conditions enabled isolation of O-heterocycles with high levels of diastereoselectivity. A variety of derivatisation reactions are also performed, generating functionalised hydroacylation products. This sequence serves as a general approach for the synthesis of fully saturated heterocycles. We demonstrate a one-pot hydroacylation/intramolecular conjugate-addition sequence to access a series of complex stereodefined heterocycles. Subsequent diversification of products is achieved, furnishing functionalized sp 3 -rich fragments.
Bibliography:	Electronic supplementary information (ESI) available. CCDC For ESI and crystallographic data in CIF or other electronic format see DOI 2091913-2091916 10.1039/d1sc06900d ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 These authors contributed equally.
ISSN:	2041-6520 2041-6539
DOI:	10.1039/d1sc06900d