ENE APPROACH TO ASYMMETRIC CATALYSIS OF THE SAKURAI-HOSOMI REACTION, LEWIS ACID-PROMOTED CARBONYL-ADDITION REACTION WITH ALLYLIC SILANES

被引：25

作者：

MIKAMI, K

MATSUKAWA, S

机构：

[1] Department of Chemical Technology, Tokyo Institute of Technology, Meguro-ku, Tokyo

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 19期

关键词：

D O I：

10.1016/S0040-4039(00)76849-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The chiral Lewis acid prepared from (R)-binaphthol and diisopropoxytitanium dichloride catalyzes the reaction of glyoxylate esters with methallylsilanes to afford mainly ene-type products rather than the products expected from the ''usual'' Sakurai-Hosomi reaction. The ene-type products lead eventually after protodesilylation to the ''usual'' products with high enantiomeric excesses.

引用

页码：3133 / 3136

页数：4

共 20 条

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Onishi, Y
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Baba, A
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (09) : 1578 - 1581
[2] Development of a chiral Lewis acid-promoted asymmetric aldol reaction using oxazaborolidinone
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[3] Asymmetric Addition of Allylsilanes to Aldehydes: A Cr/Photoredox Dual Catalytic Approach Complementing the Hosomi-Sakurai Reaction
Schaefers, Felix
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ACS CATALYSIS, 2022, 12 (19) : 12281 - 12290
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TETRAHEDRON LETTERS, 1996, 37 (21) : 3701 - 3704
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[6] STEPWISE INTRAMOLECULAR CYCLO-ADDITION OF NITRILE OXIDE EQUIVALENTS DERIVED FROM THE LEWIS ACID-PROMOTED REACTION OF 1-NITROALKADIENES AND ALLYLIC STANNANES
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[8] Lewis acid-promoted carbonyl addition of lithium (α-carbalkoxyvinyl)cuprates to aldehydes provides a novel asymmetric synthesis of β,β-disubstituted α-(hydroxyalkyl)acrylates
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