trans-1-sulfonylamino-2-isoborneolsulfonylaminocyclohexane derivatives: Excellent chiral ligands for the catalytic enantioselective addition of organozinc reagents to ketones

Forrat VL; Prieto O; Ramon DJ; Yus M

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trans-1-sulfonylamino-2-isoborneolsulfonylaminocyclohexane derivatives: Excellent chiral ligands for the catalytic enantioselective addition of organozinc reagents to ketones

机译：反式-1-磺酰基氨基-2-异冰片磺酰基氨基环己烷衍生物：出色的手性配体，可将有机锌试剂催化对映选择性地加成酮

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The catalytic enantioselective addition of different organozinc reagents (such as alkyl and aryl derivatives or in situ generated aryl, allyl alkenyl, and alkynyl derivatives obtained through different transmetallation processes) to simple ketones has been accomplished by using titanium tetra-isopropoxide and chiral ligands derived from substituted trans-1-sulfonyl amino-2-isoborneolsulfonylaminocyclohexane, producing the corresponding tertiary alcohols with enantiomeric excesses (ee) up to > 99%. A simple and efficient procedure for the synthesis of the chiral ligands used in these reactions is described.

机译：通过使用四异丙醇钛和衍生自手性配体的方法，已将不同的有机锌试剂（例如烷基和芳基衍生物或通过不同的金属转移过程获得的原位生成的芳基，烯丙基烯基和炔基衍生物）催化对映选择性加成到简单的酮上。取代的反式-1-磺酰基氨基-2-异冰片酚磺酰基氨基环己烷，生成相应的叔醇，对映体过量（ee）最高> 99％。描述了一种合成这些反应中使用的手性配体的简单有效的方法。

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《Chemistry: A European journal》 |2006年第16期|共15页
作者
Forrat VL; Prieto O; Ramon DJ; Yus M;
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正文语种 eng
中图分类化学;
关键词
alcohols; asymmetric catalysis; C-C coupling; enantioselectivity; titanium; TERTIARY HOMOALLYLIC ALCOHOLS; FACIAL-SELECTIVE ALLYLATION; ASYMMETRIC PHENYL TRANSFER; QUATERNARY CARBON CENTERS; ARYL TRANSFER-REACTIONS; BETA-AMINO ALCOHOLS; BORONIC ACIDS; METHYL KETONES; DIASTEREOSELECTIVE ADDITION; STRUCTURAL CHARACTERIZATION;

机译：醇;不对称催化;C-C偶联;对映选择性;钛;三元均烷基醇;表面选择性烯丙基化;不对称苯转移;季碳中心;芳基转移反应;BET-氨基醇;叔丁基;对苯二酸;

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1. trans-1-sulfonylamino-2-isoborneolsulfonylaminocyclohexane derivatives: Excellent chiral ligands for the catalytic enantioselective addition of organozinc reagents to ketones [J] . Forrat VL, Prieto O, Ramon DJ, Chemistry: A European journal . 2006,第16期

机译：反式-1-磺酰基氨基-2-异冰片磺酰基氨基环己烷衍生物：出色的手性配体，可将有机锌试剂催化对映选择性地加成酮
2. Commercially available neat organozincs as highly reactive reagents for catalytic enantioselective addition to ketones and aldehydes under solvent free conditions [J] . Hatano M., Mizuno T., Ishihara K. Tetrahedron . 2011,第24期

机译：市售的纯有机锌作为高反应性试剂，可在无溶剂条件下催化对映选择性加成酮和醛
3. Enantioselective Addition of Organozinc to Aldehydes and Ketones Catalyzed by Immobilized Chiral Ligands [J] . R. Somanathan L.Z. Flores-López R. Montalvo-González D. Chávez M. Parra-Hake and G. Aguirre Mini-Reviews in Organic Chemistry . 2010,第1期

机译：固定化手性配体催化有机锌对醛和酮的对映选择性加成
4. Aminohydroxyphosphine Ligand for Copper-Catalyzed Enantioselective Conjugate Addition of Organozinc Reagents [C] . Naohiko Yoshikai, Alakananda Hajra, Eiichi Nakamura Symposium on Organometallic Chemistry . 2006

机译：用于铜催化的致剂偶联缀合物的氨基羟基膦配体加入有机夹试剂
5. I. Catalytic asymmetric addition of organozinc reagents to ketones. II. Novel 1-alkenyl-1,1-bimetallic reagents: Generation and synthetic applications [D] . Li, Hongmei 2007

机译：I.有机锌试剂向酮的催化不对称加成。二。新型1-烯基-1,1-双金属试剂：生成和合成应用
6. Metal-Free Catalytic Enantioselective C–B Bond Formation: (Pinacolato)boron Conjugate Additions to αβ-Unsaturated Ketones Esters Weinreb Amides and Aldehydes Promoted by Chiral N-Heterocyclic Carbenes [O] . Hao Wu, Suttipol Radomkit, Jeannette M. O’Brien, -1

机译：金属 - 催化免不对称C-B键的形成：（频哪醇）硼共轭加成到αβ不饱和酮酯酰胺的Weinreb和醛手性N-杂环卡宾推荐
7. trans-1-Sulfonylamino-2-isoborneolsulfonylaminocyclohexane Derivatives: Excellent Chiral Ligands for the Catalytic Enantioselective Addition of Organozinc Reagents to Ketones [O] . Vincente J. Forrat, Oscar Prieto, Diego J. Ramón, 2006

机译：Trans-1-磺酰基氨基-2-异丙酚磺酰氨基环己烷衍生物：用于催化对酮的催化映选择性加入有机锌试剂的优异手性配体

trans-1-sulfonylamino-2-isoborneolsulfonylaminocyclohexane derivatives: Excellent chiral ligands for the catalytic enantioselective addition of organozinc reagents to ketones

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