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Volumn 132, Issue 6, 2010, Pages 1760-1761

Diastereo- and enantioselective anti-alkoxyallylation employing allylic gem-dicarboxylates as allyl donors via iridium-catalyzed transfer hydrogenation

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; ALIPHATIC ALDEHYDES; ALLYL ACETATE; CHEMICAL EQUATIONS; DIASTEREOSELECTIVITIES; DICARBOXYLATES; ENANTIOSELECTIVE; ISOLATED YIELD; ISOPROPYL ALCOHOLS; NITROBENZOIC ACIDS; SEGPHOS; TRANSFER HYDROGENATIONS;

EID: 77249172706     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja9097675     Document Type: Article
Times cited : (69)

References (45)
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    • For aldehyde alkoxyallylation employing alkoxy-substituted allyltitanium reagents, see: Hafner, A.; Duthaler, R. O.; Marti, R.; Rihs, G.; Rothe-Streit, P.; Schwarzenbach, F. J. Am. Chem. Soc. 1992, 114, 2321. To our knowledge, Duthaler's chirally modified allyltitanium reagent is unique in its ability to promote highly stereocontrolled "direct" anti-alkoxyallylation of aldehydes. For a highly enantioselective indirect method, see ref 8.
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    • Direct metallation of allyl ethers is Z-selective as a result of chelation. Hence, access to E-configured alkoxy-substituted allylmetal reagents and the resulting anti-1,2-diols has been problematic. For a more detailed discussion, see: Moriya, T.; Suzuki, A.; Miyaura, N. Tetrahedron Lett. 1995, 36, 1887, and refs 8 and 9c.
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    • Upon exposure of cis,trans-2,3-hexadiene to conditions for osmium-catalyzed asymmetric dihydroxylation, the trans olefin reacts preferentially to provide the syn diol. See: Xu, D.; Crispino, G. A.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7570.
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    • As described in ref 14e, preactivation refers to the degree of separation between a reagent or reactant and the parent feedstocks
    • As described in ref 14e, preactivation refers to the degree of separation between a reagent or reactant and the parent feedstock(s).
  • 30
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    • This process employs 3-chloropropenyl pivalate as the allyl donor, and only modest levels diastereo- and enantioselectivity are observed. For catalytic enantioselective aldehyde alkoxyallylation via Nozaki-Hiyama coupling, see
    • For catalytic enantioselective aldehyde alkoxyallylation via Nozaki-Hiyama coupling, see: Lombardo, M.; Licciulli, S.; Morganti, S.; Trombini, C. Chem. Commun. 2003, 1762. This process employs 3-chloropropenyl pivalate as the allyl donor, and only modest levels diastereo- and enantioselectivity are observed.
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    • For selected reviews of C-C bond-forming hydrogenation and transfer hydrogenation, see: a
    • For selected reviews of C-C bond-forming hydrogenation and transfer hydrogenation, see: (a) Ngai, M.-Y.; Kong, J. R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063.
    • (2007) J. Org. Chem , vol.72 , pp. 1063
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  • 36
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    • For enantioselective carbonyl allylation, crotylation, and tert-prenylation via iridium-catalyzed C-C bond-forming transfer hydrogenation, see: (a) Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6340.
    • For enantioselective carbonyl allylation, crotylation, and tert-prenylation via iridium-catalyzed C-C bond-forming transfer hydrogenation, see: (a) Kim, I. S.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2008, 130, 6340.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.