Catalytic enantioselective intermolecular cycloaddition of 2-diazo-3,6-diketoester-derived carbonyl ylides with alkynes and styrenes using chiral dirhodium(II) carboxylates

Organic Letters

Volumn 10, Issue 16, 2008, Pages 3603-3606

  Shimada, Naoyuki ^a   Anada, Masahiro ^a   Nakamura, Seiichi ^a   Nambu, Hisanori ^a   Tsutsui, Hideyuki ^a   Hashimoto, Shunichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZO COMPOUND; CARBOXYLIC ACID; EPOXIDE; ESTER; KETONE; ORGANOMETALLIC COMPOUND; RHODIUM; STYRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKYNES; AZO COMPOUNDS; CARBOXYLIC ACIDS; CATALYSIS; CYCLIZATION; EPOXY COMPOUNDS; ESTERS; KETONES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RHODIUM; STEREOISOMERISM; STYRENES;

EID: 54049087840     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8013733     Document Type: Article

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49. 4 (3) in hexane at 25 °C provided cycloadduct 6a in 41% yield with 61% ee. See ref 13.
50. The preferred absolute stereochemistry of cycloadducts was not determined.
51. 4, was developed by Reddy and Davies: Reddy, R. P.; Davies, H. M. L. Org. Lett. 2006, 8, 5013-5016.
52. 2, 14% yield, 40% ee.
53. For the orbital correlation diagram, see the Supporting Information.
54. The use of p-nitrophenylacetylene as a strongly electron-deficient dipolarophile resulted in 17% yield of cycloadduct with 72% ee.
55. 4 (2) in hexane at 20 °C increased exo diastereoselectivity (exo: endo = 10:1, 73% yield) and provided 61% ee for exo cycloadduct 8a. See ref 13b.
56. 4 was less effective for the reaction of 4a with DMAD, giving the corresponding cycloadduct in 60% yield with 40% ee.
57. Very recently, Suga and co-workers have reported highly enantioselective dipole-LUMO/dipolarophile-HOMO controlled cycloadditions between 2-benzopyrylium-4-olates and vinyl ether derivatives using chiral Lewis acid catalysts: Suga, H.; Ishimoto, D.; Higuchi, S.; Ohtsuka, M.; Arikawa, T.; Tsuchida, T.; Kakehi, A.; Baba, T. Org. Lett. 2007, 9, 4359-4362.