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Volumn 48, Issue 27, 1992, Pages 5719-5730

Enantioselective preparation of sec. Alcohols from aldehydes and dialkyl zinc compounds, generated in situ from Grignard reagents, using substoichiometric amounts of TADDOL-titanates

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EID: 0000969786     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(92)80023-9     Document Type: Article
Times cited : (162)

References (82)
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    • Preliminary communication
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  • 18
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    • [2+2] Cycloadditions
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  • 19
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    • Asymmetric (2+2) cycloaddition reaction between .ALPHA., .BETA.-unsaturated acid derivatives and alkynyl or alkenyl sulfides catalyzed by a chiral titanium reagent.
    • (1990) Chemistry Letters , pp. 1295-1298
    • Hayashi1    Narasaka2
  • 23
    • 0002098511 scopus 로고
    • Katalytische und stöchiometrische enantioselektive Additionen von Diethylzink an Aldehyde mit Hilfe eines neuartigen chiralen Spirotitanats
    • (1991) Angewandte Chemie , vol.103 , pp. 100-101
    • Schmidt1    Seebach2
  • 27
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    • Enantioselektive Addition von Organometallreagentien an Carbonylverbindungen: Übertragung, Vervielfältigung und Verstärkung der Chiralität
    • For an up to date review see
    • (1991) Angewandte Chemie , vol.103 , pp. 34-55
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  • 37
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    • Catalytic asymmetric synthesis ofSecondary (E)-allyl alcohols from acetylenes and aldehydesvia (1-alkenyl)zinc intermediates. Preliminary Communication
    • (1992) Helvetica Chimica Acta , vol.75 , pp. 170-173
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  • 50
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    • 2 (filtration after addition of 1.3 equiv. dioxan) or from Zn and RI in THF also gave satisfactory enantioselectivities (82 – 96% ee with R = Et, Pr, Bu) following the procedure described in section B, but the reaction was very slow and gave poor yields even after 50 h at −15°C.
  • 51
    • 84918186503 scopus 로고    scopus 로고
    • Allylzinc reagents show quantitative conversion to the product alcohols, but fail to give any enantioselectivity, while benzylzinc reagents react extremely sluggishly and unselectively.
  • 54
    • 84918186502 scopus 로고
    • Enantiomeric ratios of only 4:1 could be reached with salt-free Reformatzky-type reagents under various conditions
    • (1991) Diplomarbeit ETH-Zürich
    • Kaufmann1
  • 55
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    • Similarly alkynyl- and furanylzinc reagents showed disappointingly low (58 : 42 and 40 : 60 resp.) enantioselectivities.
  • 63
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    • CVII.?Investigations on the dependence of rotatory power on chemical constitution. Part VI. The optical rotatory power of methyl-tert.-butyl-, methylbenzyl-, methylphenylethyl- and methyl-?-naphthyl-carbinols
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  • 72
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    • Beilsteins Handbuch der Organischen Chemie, Vol. 6 (II) p. 510.
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    • Beilsteins Handbuch der Organischen Chemie, Vol. 6 (III) p. 175.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.