Chiral NHC-catalyzed Oxodiene Diels-Alder Reactions with Alpha-chloroaldehyde Bisulfite Salts

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2008 Jul 29

PMID 18656948

Citations 12

Authors

Ming He

Brendan J Beahm

Jeffrey W Bode

Affiliations

Soon will be listed here.

Abstract

Alpha-chloroaldehyde bisulfite adducts were successfully employed in chiral NHC-catalyzed hetero-Diels-Alder reactions with various oxodienes under biphasic reaction conditions with high levels of enantioselectivity. This new protocol makes possible enantioselective additions from commercially available chloroacetaldehyde sodium bisulfite and demonstrates that this unique class of catalysts readily tolerates aqueous conditions.

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References

Abraham C, Paull D, Scerba M, Grebinski J, Lectka T . Catalytic, enantioselective bifunctional inverse electron demand hetero-Diels-Alder reactions of ketene enolates and o-benzoquinone diimides. J Am Chem Soc. 2006; 128(41):13370-1. DOI: 10.1021/ja065754d. View

Chow K, Bode J . Catalytic generation of activated carboxylates: direct, stereoselective synthesis of beta-hydroxyesters from epoxyaldehydes. J Am Chem Soc. 2004; 126(26):8126-7. DOI: 10.1021/ja047407e. View

Jarvo E, Lawrence B, Jacobsen E . Highly enantio- and regioselective quinone Diels-Alder reactions catalyzed by a tridentate [(Schiff Base)Cr(III)] complex. Angew Chem Int Ed Engl. 2005; 44(37):6043-6. DOI: 10.1002/anie.200502176. View

Seki M, Hatsuda M, Mori Y, Yoshida S, Yamada S, Shimizu T . A practical synthesis of (+)-biotin from L-cysteine. Chemistry. 2004; 10(23):6102-10. DOI: 10.1002/chem.200400733. View

Corey E . Catalytic enantioselective Diels--Alder reactions: methods, mechanistic fundamentals, pathways, and applications. Angew Chem Int Ed Engl. 2009; 41(10):1650-67. DOI: 10.1002/1521-3773(20020517)41:10<1650::aid-anie1650>3.0.co;2-b. View

Hayashi Y, Itoh T, Ohkubo M, Ishikawa H . Asymmetric Michael reaction of acetaldehyde catalyzed by diphenylprolinol silyl ether. Angew Chem Int Ed Engl. 2008; 47(25):4722-4. DOI: 10.1002/anie.200801130. View

Phillips E, Wadamoto M, Chan A, Scheidt K . A highly enantioselective intramolecular Michael reaction catalyzed by N-heterocyclic carbenes. Angew Chem Int Ed Engl. 2007; 46(17):3107-10. PMC: 2978499. DOI: 10.1002/anie.200605235. View

He M, Bode J . Enantioselective, NHC-catalyzed bicyclo-beta-lactam formation via direct annulations of enals and unsaturated N-sulfonyl ketimines. J Am Chem Soc. 2007; 130(2):418-9. DOI: 10.1021/ja0778592. View

Garcia-Garcia P, Ladepeche A, Halder R, List B . Catalytic asymmetric Michael reactions of acetaldehyde. Angew Chem Int Ed Engl. 2008; 47(25):4719-21. DOI: 10.1002/anie.200800847. View

10.

Nicolaou K, Snyder S, Montagnon T, Vassilikogiannakis G . The Diels--Alder reaction in total synthesis. Angew Chem Int Ed Engl. 2009; 41(10):1668-98. DOI: 10.1002/1521-3773(20020517)41:10<1668::aid-anie1668>3.0.co;2-z. View

11.

Esquivias J, Arrayas R, Carretero J . Catalytic asymmetric inverse-electron-demand Diels-Alder reaction of N-sulfonyl-1-aza-1,3-dienes. J Am Chem Soc. 2007; 129(6):1480-1. DOI: 10.1021/ja0658766. View

12.

Alcaide B, Almendros P . Organocatalytic reactions with acetaldehyde. Angew Chem Int Ed Engl. 2008; 47(25):4632-4. DOI: 10.1002/anie.200801231. View

13.

Reynolds N, Read de Alaniz J, Rovis T . Conversion of alpha-haloaldehydes into acylating agents by an internal redox reaction catalyzed by nucleophilic carbenes. J Am Chem Soc. 2004; 126(31):9518-9. DOI: 10.1021/ja046991o. View

14.

Li C . Organic reactions in aqueous media with a focus on carbon-carbon bond formations: a decade update. Chem Rev. 2005; 105(8):3095-165. DOI: 10.1021/cr030009u. View

15.

Sohn S, Rosen E, Bode J . N-heterocyclic carbene-catalyzed generation of homoenolates: gamma-butyrolactones by direct annulations of enals and aldehydes. J Am Chem Soc. 2004; 126(44):14370-1. DOI: 10.1021/ja044714b. View

16.

Hayashi Y, Itoh T, Aratake S, Ishikawa H . A diarylprolinol in an asymmetric, catalytic, and direct crossed-aldol reaction of acetaldehyde. Angew Chem Int Ed Engl. 2008; 47(11):2082-4. DOI: 10.1002/anie.200704870. View

17.

He M, Bode J . Catalytic Synthesis of gamma-Lactams via direct annulations of enals and N-sulfonylimines. Org Lett. 2005; 7(14):3131-4. DOI: 10.1021/ol051234w. View

18.

Evans D, Olhava E, Johnson J, Janey J . Chiral C -Symmetric Cu Complexes as Catalysts for Enantioselective Hetero-Diels-Alder Reactions. Angew Chem Int Ed Engl. 2018; 37(24):3372-3375. DOI: 10.1002/(SICI)1521-3773(19981231)37:24<3372::AID-ANIE3372>3.0.CO;2-K. View

19.

Itoh J, Fuchibe K, Akiyama T . Chiral Brønsted acid catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with imines. Angew Chem Int Ed Engl. 2006; 45(29):4796-8. DOI: 10.1002/anie.200601345. View

20.

Zhang Y, He L, Wu X, Shao P, Ye S . Chiral N-heterocyclic carbene catalyzed staudinger reaction of ketenes with imines: highly enantioselective synthesis of N-Boc beta-lactams. Org Lett. 2007; 10(2):277-80. DOI: 10.1021/ol702759b. View