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Rapid stereocontrolled assembly of the fully substituted C-aryl glycoside of kendomycin with a Prins cyclization: a formal synthesis.通过普林斯环化反应快速立体控制组装肯多霉素的全取代C-芳基糖苷：形式合成
Chem Commun (Camb). 2006 Jun 14(22):2388-90. doi: 10.1039/b602937j. Epub 2006 May 2.
2
Solvolysis of a tetrahydropyranyl mesylate: mechanistic implications for the Prins cyclization, 2-oxonia-cope rearrangement, and Grob fragmentation.甲磺酸四氢吡喃酯的溶剂解：对普林斯环化、2-氧杂环戊二烯重排和格罗布碎片化反应机理的启示
Org Lett. 2006 May 11;8(10):2175-8. doi: 10.1021/ol0606738.
3
Synthesis and structure revision of calyxin natural products.卡里辛天然产物的合成与结构修正
J Org Chem. 2006 Apr 14;71(8):3176-83. doi: 10.1021/jo060094g.
4
The silylalkyne-Prins cyclization: stereoselective synthesis of tetra- and pentasubstituted halodihydropyrans.硅烷基炔丙基环化反应：四取代和五取代卤代二氢吡喃的立体选择性合成
Org Lett. 2006 Apr 13;8(8):1633-6. doi: 10.1021/ol060247m.
5
New chiral synthons for efficient introduction of bispropionates via stereospecific oxonia-cope rearrangements.用于通过立体定向氧鎓-科普重排高效引入双丙酸酯的新型手性合成子。
J Am Chem Soc. 2006 Apr 12;128(14):4568-9. doi: 10.1021/ja061082f.
6
Scope and facial selectivity of the Prins-pinacol synthesis of attached rings.连接环的普林斯-频哪醇合成的范围和面部选择性。
J Org Chem. 2006 Feb 17;71(4):1581-7. doi: 10.1021/jo0522862.
7
Syn- and anti-selective Prins cyclizations of delta,epsilon-unsaturated ketones to 1,3-halohydrins with Lewis acids.δ,ε-不饱和酮与路易斯酸发生的对映选择性和顺式选择性普林斯环化反应生成1,3-卤代醇。
J Org Chem. 2006 Feb 17;71(4):1493-501. doi: 10.1021/jo052142n.
8
Tetrahydropyran rings from a Mukaiyama-Michael cascade reaction.来自向山-迈克尔串联反应的四氢吡喃环。
J Am Chem Soc. 2005 Nov 23;127(46):16044-5. doi: 10.1021/ja056483u.
9
Total synthesis of a diastereomer of the marine natural product clavosolide A.海洋天然产物克拉沃索利德A非对映异构体的全合成。
Chem Commun (Camb). 2005 Oct 28(40):5097-9. doi: 10.1039/b509757f. Epub 2005 Sep 15.
10
Prins cyclizations in silyl additives with suppression of epimerization: versatile tool in the synthesis of the tetrahydropyran backbone of natural products.硅烷基添加剂中抑制差向异构化的普林斯环化反应：天然产物四氢吡喃骨架合成中的通用工具。
Org Lett. 2005 Sep 29;7(20):4491-4. doi: 10.1021/ol051951q.

普林斯环化反应中的外消旋化

Racemization in Prins cyclization reactions.

作者信息

Jasti Ramesh, Rychnovsky Scott D

机构信息

Department of Chemistry, University of California-Irvine, 1102 Natural Sciences II, Irvine, CA 92697-2025, USA.

出版信息

J Am Chem Soc. 2006 Oct 18;128(41):13640-8. doi: 10.1021/ja064783l.

DOI:10.1021/ja064783l
PMID:17031979
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC2483253/
Abstract

Isotopic labeling experiments were performed to elucidate a new mechanism for racemization in Prins cyclization reactions. The loss in optical activity for these reactions was shown to occur by 2-oxonia-Cope rearrangements by way of a (Z)-oxocarbenium ion intermediate. Reaction conditions such as solvent, temperature, and the nucleophile employed played a critical role in whether an erosion in enantiomeric excess was observed. Additionally, certain structural features of Prins cyclization precursors were also shown to be important for preserving optical purity in these reactions.

摘要

进行了同位素标记实验，以阐明普林斯环化反应中消旋化的新机制。这些反应中旋光活性的丧失被证明是通过（Z）-氧鎓离子中间体经2-氧杂环丁烷-科普重排发生的。诸如溶剂、温度和所用亲核试剂等反应条件，对于是否观察到对映体过量的降低起着关键作用。此外，普林斯环化前体的某些结构特征对于在这些反应中保持光学纯度也很重要。