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卤代乙烯基硼烷：一类新型的狄尔斯-阿尔德亲双烯体。

Alkylhalovinylboranes: a new class of Diels-Alder dienophiles.

作者信息

Pisano Pablo L, Pellegrinet Silvina C

机构信息

Instituto de Química Rosario (CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario Suipacha 531 Rosario (2000) Argentina

出版信息

RSC Adv. 2018 Oct 2;8(59):33864-33871. doi: 10.1039/c8ra07089j. eCollection 2018 Sep 28.

DOI:10.1039/c8ra07089j
PMID:35548792
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9086730/
Abstract

The Diels-Alder reactions of alkylhalovinylboranes have been investigated theoretically and experimentally. Alkylhalovinylboranes presented higher reactivity than the corresponding dialkylvinylboranes. Although / selectivities were high for the reactions with cyclopentadiene, facial selectivities for the chiral analogues were low. Our results demonstrate that the replacement of an alkyl group on the boron atom by a halogen increases the dienophilicity considerably.

摘要

对卤代乙烯基硼烷的狄尔斯-阿尔德反应进行了理论和实验研究。卤代乙烯基硼烷比相应的二烷基乙烯基硼烷具有更高的反应活性。尽管与环戊二烯反应的选择性很高，但手性类似物的面选择性较低。我们的结果表明，硼原子上的一个烷基被卤素取代会显著增加亲双烯体活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/21ff30b758f5/c8ra07089j-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/9d722970cdef/c8ra07089j-s1.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/b1bc1052049d/c8ra07089j-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/ef4bc7d016da/c8ra07089j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/3a87de443f70/c8ra07089j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/652fb97c849d/c8ra07089j-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/a6cff2265fde/c8ra07089j-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/c507b18fc20c/c8ra07089j-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/cd9c0bab0c4d/c8ra07089j-s5.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/02072403a53c/c8ra07089j-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/21ff30b758f5/c8ra07089j-s7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/9d722970cdef/c8ra07089j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/c5ba3ade626d/c8ra07089j-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/b1bc1052049d/c8ra07089j-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/ef4bc7d016da/c8ra07089j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/3a87de443f70/c8ra07089j-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/652fb97c849d/c8ra07089j-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/a6cff2265fde/c8ra07089j-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/c507b18fc20c/c8ra07089j-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/cd9c0bab0c4d/c8ra07089j-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/9ac9c9483e54/c8ra07089j-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/02072403a53c/c8ra07089j-s6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/f63e/9086730/21ff30b758f5/c8ra07089j-s7.jpg

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