Facial diastereoselectivity in cationic propargylations with planar-chiral areneCr(CO)3-substituted propargyl cations

被引：10
|
作者：
Netz, A
Polborn, K
Nöth, H
Müeller, TJJ
机构：
[1] Univ Munich, Dept Chem, D-81377 Munich, Germany
[2] Abbott GmbH & Co KG, D-67061 Ludwigshafen, Germany
[3] Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 2005卷 / 09期
关键词：
addition reactions; alkynes; arenes; chromium; diastereoselectivity;
D O I：
10.1002/ejoc.200400798
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The planar-chiral (o-methoxyphenyl) chromium tricarbonyl-substituted propargyl cation 4 reacts with silyl enol ether derivatives 5 with poor and with enamines 6 with good facial diastereoselectivity to give rise to the (arene)carbonylchromium-substituted propargylated cyclohexan-2-ones 7 and 8, carboxylic acid 9, gamma-lactone 10, cyclopentan-2-one 11, and esters 16 and 17. Structural correlations were unambiguously deduced from X-ray structure analyses of 7a, 9a, and 17a. The origin of facial diastereoselectivity with this class of organometallic electrophiles lies in steric and stereoelectronic biases rather than in purely electronic nucleophilicity. (c) Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：1823 / 1833
页数：11
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