+ Site Statistics
References:
54,258,434
Abstracts:
29,560,870
PMIDs:
28,072,757
+ Search Articles
+ PDF Full Text Service
How our service works
Request PDF Full Text
+ Follow Us
Follow on Facebook
Follow on Twitter
Follow on LinkedIn
+ Subscribe to Site Feeds
Most Shared
PDF Full Text
+ Translate
+ Recently Requested

Indium(III)-catalyzed asymmetric hetero-Diels-Alder reaction of Brassard-type diene with aliphatic aldehydes



Indium(III)-catalyzed asymmetric hetero-Diels-Alder reaction of Brassard-type diene with aliphatic aldehydes



Organic Letters 13(15): 3868-3871



A highly diastereo- and enantioselective hetero-Diels-Alder (HDA) reaction of a Brassard-type diene with aliphatic aldehydes has been developed. The chiral N,N'-dioxide L2/In(OTf)(3) complex was efficient toward the obtention of the corresponding β-methoxy-γ-methyl α,β-unsaturated δ-lactones in good yields (up to 86%) as well as dr and ee values (up to 97:3 cis/trans and 94% ee). In addition, the product 4a could be easily transformed into the methyl-protected epi-prelactone B by hydrogenation.

Please choose payment method:






(PDF emailed within 0-6 h: $19.90)

Accession: 053815166

Download citation: RISBibTeXText

PMID: 21707114

DOI: 10.1021/ol2013999


Related references

Efficient enantioselective hetero-Diels-Alder reaction of Brassard's diene with aliphatic aldehydes: a one-step synthesis of (R)-(+)-kavain and (S)-(+)-dihydrokavain. Organic Letters 10(6): 1311-1314, 2008

Highly enantioselective hetero-Diels-Alder reaction of Brassard diene with aromatic aldehydes. Organic Letters 6(13): 2185-2188, 2004

Enantioselective catalysis of the hetero-Diels-Alder reaction between Brassard's diene and aldehydes by hydrogen-bonding activation: a one-step synthesis of (S)-(+)-dihydrokawain. Chemistry 10(23): 5964-5970, 2004

Magnesium(II)-catalyzed asymmetric hetero-Diels-Alder reaction of Brassard's dienes with isatins. Chemical Communications 50(8): 994-996, 2014

Highly enantioselective hetero- Diels-Alder reaction of trans-1-methoxy- 2-methyl-3-trimethylsiloxybuta-1,3-diene with aromatic and aliphatic aldehydes catalyzed by 3-substituted BINOL-titanium complex. Organic Letters 10(6): 1299-1302, 2008

Asymmetric Hetero-Diels-Alder Reactions of Danishefsky's and Brassard's Dienes with Aldehydes. Synlett 2007(14): 2147-2157, 2007

N-heterocyclic-carbene-catalyzed asymmetric oxidative hetero-Diels-Alder reactions with simple aliphatic aldehydes. Angewandte Chemie 51(49): 12330-3, 2013

Synthesis of Optically Pure Spiro[cyclohexane-oxindoline] Derivatives via Catalytic Asymmetric Diels-Alder Reaction of Brassard-Type Diene with Methyleneindolines. Journal of Organic Chemistry 80(17): 8836-8842, 2015

The asymmetric hetero-Diels-Alder reaction of enamide aldehydes with Danishefsky's diene and an efficient synthesis of chiral binaphthyl ligands. Tetrahedron Letters 41(14): 2327-2331, April 1, 2000

Theoretical investigations on the mechanism of hetero-Diels-Alder reactions of Brassard's diene and 1, 3-butadiene catalyzed by a tridentate schiff base titanium(IV) complex. Chemistry 16(14): 4359-4367, 2010

A highly enantioselective hetero-Diels-Alder reaction of aldehydes with Danishefsky's diene catalyzed by chiral titanium(IV) 5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol complexes. Journal of Organic Chemistry 67(7): 2175-2182, 2002

Montmorillonite K10-Catalyzed Aza Diels-Alder Reaction of Danishefskys Diene with Aldimines, Generated in situ from Aliphatic Aldehydes and Amine, in Aqueous Media. Synlett 2002(11): 1898-1900, 2002

Chiral Brønsted acid catalyzed enantioselective aza-Diels-Alder reaction of Brassard's diene with imines. Angewandte Chemie 45(29): 4796-4798, 2006

Asymmetric hetero-Diels-Alder reaction of Danishefsky's diene with α-ketoesters and isatins catalyzed by a chiral N,N'-dioxide/magnesium(II) complex. Chemistry 20(44): 14493-8, 2014

Asymmetric hetero-Diels-Alder reaction of Danishefsky's dienes with α-carbonyl esters catalyzed by an indium(III)-pybox complex. Organic Letters 15(12): 2914-2917, 2013