1427054-10-1Relevant articles and documents
Catalytic asymmetric synthetic method for chiral spirodiol derivative
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Paragraph 0215; 0216; 0217; 0218; 0219, (2017/08/02)
The invention belongs to the field of organic synthesis, and discloses a catalytic asymmetric synthetic method for a chiral spirodiol derivative. The catalytic asymmetric synthetic method comprises the following step: with chiral phosphoric acid as a catalyst, subjecting a compound as shown in a formula I in the specification and/or a compound as shown in a formula II in the specification to a reaction so as to obtain a product. In the formula I and the formula II, R1, R2, R4, R5, R6 and R7 are independently selected from any groups; and R3 is an alkyl group. The catalytic asymmetric synthetic method is a convenient, rapid and direct method for construction of a chiral spirodiol structure. The synthetic method provided by the invention has the advantages of high yield, good enantioselectivity, capability of tolerating a variety of functional groups, etc., can reduce the usage amount of the catalyst to 0.1 mol% during large-scale synthesis, and has application values in industrial production.
Phosphoric Acid-Catalyzed Asymmetric Synthesis of SPINOL Derivatives
Li, Shaoyu,Zhang, Ji-Wei,Li, Xian-Lin,Cheng, Dao-Juan,Tan, Bin
, p. 16561 - 16566 (2016/12/27)
Axially chiral 1,1′-spirobiindane-7,7′-diol (SPINOL) is the most fundamental and important privileged structure from which other chiral ligands containing a 1,1′-spirobiindane backbone are synthesized. Driven by the development of enantioselective syntheses of axially chiral SPINOL derivatives, we have successfully developed the first phosphoric acid-catalyzed asymmetric approach. This approach is highly convergent and functional group tolerant, efficiently providing SPINOLs in good yield with excellent enantioselectivity, thus delivering a practical and straightforward access to this privileged structure. It should be emphasized that the catalyst loading could be decreased to only 0.1 mol% for the preparative-scale synthesis. Furthermore, 4,4′-dimethyl-SPINOL-phosphoric acid was synthesized and applied to catalyze the model reaction for synthesis of enantioenriched SPINOL derivatives.