Isolation and enantiostability of the B-chiral bis(salicylato) borate anions [B-R(Sal)(2)] and [B-S(Sal)(2)]

Wong Lawrence W. -Y.; Au Yeung Alex S. -F.; Tam Gemma S. -S.; Kan Jack W. -H.; Sung Herman H. -Y.; Sheong Fu Kit; Lin Zhenyang; Williams Ian D.

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Isolation and enantiostability of the B-chiral bis(salicylato) borate anions [B-R(Sal)(2)] and [B-S(Sal)(2)]

机译：B-chiral双（水杨酸盐）硼酸盐阴离子[B-R（SAL）（2）]和[B-S（SAL）（2）]的分离和对抗性。

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The chiral spiroborate anions [B-S(Sal) (]) and [B-R(Sal)(2)], (R and S subscripts indicate boron stereochemistry) have been isolated as 1 : 1 quininium and 1 : 2 sparteinium salts, [HQuin][B-S(Sal)(2)] and [H(2)Spa][B-R(Sal)(2)](2) respectively, by either cation metathesis or a simple one-pot synthesis involving reaction of boric and salicylic acids with the alkaloid base. Circular dichroism (CD) spectroscopy shows that the B-based chirality is stable in polar aprotic media, such as DMF or DMSO, though labile in protic solutions. Enantiopure salts with achiral counter-cations such as [NBu4][B-R(Sal)(2)] may then be prepared by exchange, so these B-chiral anions may have use in metathesis-based resolutions. Due to a site disorder the anion in [H(2)Spa][B-R(Sal)(2)](2) is limited to 70% ee, however an enantiopure analogue [H(2)Spa][B-R(5-Cl-Sal)(2)](2) is readily formed using 5-chlorosalicylic acid. This also indicates a wide family of stable enantiopure B-chiral anions may be isolated by this approach.

机译：手性螺旋硼酸阴离子[BS（SAL）（]）和[Br（SAL）（2）]，（R和S下标表明硼立体化学）已被分离为1：1奎尼昂和1：2 Sparteinium Salts，[HQuin] [BS（SAL）（2）]和[H（2）SPA] [Br（SAL）（2）]（2）分别通过阳离子复分解或涉及硼酸和水杨酸反应的简单的单盆合成生物碱基础。圆形二色性（CD）光谱表明，B基的性儿童在极性非质介质中稳定，例如DMF或DMSO，但在质子溶液中的不稳定。然后通过交换制备诸如[NBU4] [B-R（SAL）（2）]之类的甲状腺反阳离子的对映络盐，因此这些B-Chiral阴离子可用于复分解的分辨率。由于部位障碍[H（2）Spa] [Br（SAL）（2）]（2）的阴离子限制在70％EE中，但是对映形式[H（2）SPA] [BR（5-使用5-氯化铵酸容易地形成C1- SA1）（2）。这也表明可以通过这种方法分离广泛的稳定对映阴离子。

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《RSC Advances》 |2018年第3期|共10页
作者
Wong Lawrence W. -Y.; Au Yeung Alex S. -F.; Tam Gemma S. -S.; Kan Jack W. -H.; Sung Herman H. -Y.; Sheong Fu Kit; Lin Zhenyang; Williams Ian D.;
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Hong Kong Univ Sci &

Technol Dept Chem Kowloon Hong Kong Peoples R China;

Hong Kong Univ Sci &

Technol Dept Chem Kowloon Hong Kong Peoples R China;

Hong Kong Univ Sci &

Technol Dept Chem Kowloon Hong Kong Peoples R China;

Hong Kong Univ Sci &

Technol Dept Chem Kowloon Hong Kong Peoples R China;

Hong Kong Univ Sci &

Technol Dept Chem Kowloon Hong Kong Peoples R China;

Hong Kong Univ Sci &

Technol Dept Chem Kowloon Hong Kong Peoples R China;

Hong Kong Univ Sci &

Technol Dept Chem Kowloon Hong Kong Peoples R China;

Hong Kong Univ Sci &

Technol Dept Chem Kowloon Hong Kong Peoples R China;

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正文语种 eng
中图分类化学;
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1. Isolation and enantiostability of the B-chiral bis(salicylato) borate anions [B-R(Sal)(2)] and [B-S(Sal)(2)] [J] . Wong Lawrence W. -Y., Au Yeung Alex S. -F., Tam Gemma S. -S., RSC Advances . 2018,第3期

机译：B-chiral双（水杨酸盐）硼酸盐阴离子[B-R（SAL）（2）]和[B-S（SAL）（2）]的分离和对抗性。
2. The synthesis,the spectral and structural characterization of two new compounds of the series [Cu(sal)(AA)(ClO_4)] (sal=anion of the salicylaldehyde,AA=4,4'-dimethyl-2,2'-bispyridil and 2,2'-bispyrimidine) [J] . Augustin M.Madalan, Elena Melnic, Victor Ch.Kravtsov, Revista de Chimie . 2004,第9期

机译：[Cu（sal）（AA）（ClO_4）]系列的两种新化合物的合成，光谱和结构表征（sal =水杨醛的阴离子，AA = 4,4'-二甲基-2,2'-双吡啶和2,2'-双嘧啶）
3. The synthesis,the spectral and structural characterization of two new compounds of the series [Cu(sal)(AA)(ClO_4)] (sal=anion of the salicylaldehyde,AA=4,4'-dimethyl-2,2'-bispyridil and 2,2'-bispyrimidine) [J] . Augustin M.Madalan, Elena Melnic, Victor Ch.Kravtsov, Revista de Chimie . 2004,第9期

机译：合成，两种串联新化合物的合成，光谱和结构表征[Cu（sal）（aa）（clo_4）]（Sal =水杨醛的阴离子，Aa = 4,4'-二甲基-2,2'-双吡啶和2,2'-bispyrimidine）
4. Comparison of RNAPro center dot SAL? Saliva Collection Versus Centrifugation for Cell-Free DNA Isolation from Saliva Specimens [C] . Paul D. Slowey, U. Giese, M. Hofner, International Molecular Medicine Tri-Conference. . 2015

机译：RNAPRO中心点SAL的比较？ Saliva收集与唾液标本的无细胞DNA分离的离心
5. The SAL1 gene of Arabidopsis encoding an enzyme with 3(2)5-bisphosphate nucleotidase and inositol polyphosphate 1-phosphatase activities increases salt tolerance in yeast. [O] . F J Quintero, B Garciadeblás, A Rodríguez-Navarro 1996

机译：拟南芥的SAL1基因编码具有3（2）5-双磷酸核苷酸酶和肌醇多磷酸1-磷酸酶活性的酶可提高酵母的耐盐性。
6. Heterobimetallic Bi(III)-Ti(IV) Coordination Complexes: Synthesis and Solid-State Structures of BiTi4(sal)6(m-OiPr)3(OiPr)4, and the Cyclic Isomers Bi4Ti4(sal)10(m-OiPr)4(OiPr)4 and Bi8Ti8(sal)20(m-OiPr)8(OiPr)8 [O] . -1

机译：异质物质Bi（III）-ti（IV）配位复合物：Biti4（SAL）6（M-OIPR）3（OIPR）4的合成和固态结构，以及环状异构体Bi4Ti4（SAL）10（M-OIPR） 4（OIPR）4和Bi8Ti8（SAL）20（M-OIPR）8（OIPR）8
7. Geology for Planning: Guadalupe and Point Sal 7 1/2' Quadrangles, Santa Barbara and San Luis Obispo Counties, California. Open File Report 80-5 SF. [R] . Kilbourne, R. T., Mualchin, L. 1980

机译：规划地质：瓜达卢佩和point sal 7 1/2'四合院，圣巴巴拉和圣路易斯奥比斯波县，加利福尼亚州。打开文件报告80-5 sF。

Isolation and enantiostability of the B-chiral bis(salicylato) borate anions [B-R(Sal)(2)] and [B-S(Sal)(2)]

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