Chiral phosphoric acid with spiroindane skeleton as well as preparation method and application thereof

• Main Authors: LI SHAOYU, TAN BIN, DING WEIYI
• Format: Patent
• Language: Chinese; English
• Published: 05.06.2020
• Subjects: ACYCLIC OR CARBOCYCLIC COMPOUNDS; ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOIDCHEMISTRY; CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY; PERFORMING OPERATIONS; PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL; THEIR RELEVANT APPARATUS; TRANSPORTING

The invention belongs to the field of organic synthesis, and discloses chiral phosphoric acid with a spiroindane skeleton, which has a structure shown as a general formula I, in the formula I, Ar is one of alkyl, cyclohexyl, methoxy, trifluoromethyl, fluorine, nitro and phenyl, and m is an integer of 1-5. The chiral phosphoric acid with a novel structure is constructed, the variety of chiral phosphoric acid catalysts is enriched, and compared with existing chiral phosphoric acid, the chiral phosphoric acid has more excellent enantioselectivity in catalysis of asymmetric reaction. The inventionfurther discloses a preparation method of the chiral phosphoric acid. The preparation method comprises the step of resolving a raceme compound by utilizing cinchona alkaloid salt. 本发明属于有机合成领域，公开了一种具有螺二氢茚骨架的手性磷酸，其具有通式Ⅰ的结构：其中，Ar为R选自烷基、环己基、甲氧基、三氟甲基、氟、硝基、苯基中的一种，m表示1～5的整数。本发明构建了一类结构新颖的手性磷酸，丰富了手性磷酸催化剂的种类，与现有手性磷酸相比，本发明的手性磷酸在催化不对称反应方面具有更优异的对映选择性。本发明还公开了手性磷酸的制备方法，其步骤包括利用金鸡纳碱盐来拆分外消旋体化合物。