Method for preparing high allyl alcohol compound

A compound, alkenyl technology, applied in the field of preparation of high allyl alcohol compounds, can solve problems such as limited

Active Publication Date: 2019-04-16
盐城锦明药业有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, while many major metals, such as Li, Mg, Al, Zn, Mn, Sn, and In, have been widely used as mediators for various organic transformations, the use of iron metals as promoters for organic reactions is rather limited.

Method used

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  • Method for preparing high allyl alcohol compound
  • Method for preparing high allyl alcohol compound
  • Method for preparing high allyl alcohol compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066]

[0067] Iron powder (83.8 mg, 1.5 mmol) and DMSO (1 mL) were added sequentially to a 10 mL Schlenk bottle. The iron was then activated by adding 1,2-dibromoethane (14.1 mg, 5 mol%) and TMSCl (8.1 mg, 5 mol%). With stirring, BiCl was sequentially added to the reaction mixture 3 (31.5 mg, 0.1 mmol), 2a (241.5 mg, 1.5 mmol) and 1a (82 mg, 0.5 mmol). The suspension was stirred vigorously at room temperature for 24 h, then washed with saturated NaHCO 3 The aqueous solution was quenched. use NH 4 Cl solution (30 mL) was washed, and extracted with ethyl acetate (20 mL×3). The combined extracts were washed with brine (30 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography using ethyl acetate / petroleum ether as eluent to obtain 118.08 mg of 3a with a yield of 96% and a dr value >99:1.

Embodiment 2

[0069] According to the method of Example 1, the catalysts in the table were used to prepare 3a.

[0070]

Embodiment 3

[0072] 3a was prepared according to the method of Example 1 using the metals in the table.

[0073] Metal

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PUM

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Abstract

The invention relates to a method for preparing a high allyl alcohol compound. An effective metal-mediated highly diastereoselective allylation reaction of a carbonyl compound with allyl halide is mainly provided, a corresponding high allyl alcohol is obtained, a yield is good, and the compound has excellent diastereoselectivity and broad functional group tolerance.

Description

technical field [0001] The invention belongs to the field of chemical industry and medicine, and relates to a preparation method of homoallyl alcohol compounds. Background technique [0002] Homoallyl alcohol compounds are an important class of chemical substances, and are important intermediates for the synthesis of certain natural products, drugs, spices and pesticides. [0003] There are many methods for preparing homoallyl alcohol compounds in the prior art, but most of them have low reaction yields, cumbersome post-reaction treatment, difficult separation and purification, and poor stereoselectivity. Knochel et al. (Angew.Chem., Int.Ed., 2010, 49, 8516) reported the reaction of two highly diastereoselective carbonyl compounds with preformed cyclic allyl zinc or aluminum reagents under strictly anhydrous conditions. The following allylation reaction produces homoallylic alcohols with excellent stereoisomerism. [0004] However, while many major metals, such as Li, Mg, ...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/76C07C253/30C07C29/38C07C33/50C07C33/34C07D333/16C07D209/38C07D213/61C07C51/353C07C59/54
CPCC07C29/38C07C51/353C07C67/343C07C253/30C07D209/38C07D213/61C07D333/16C07C69/76C07C255/53C07C33/50C07C33/34C07C59/54
Inventor 冯雪馨杨锦明沈志良杨子健王庆东邱悦胡朝俊赵玉军
Owner 盐城锦明药业有限公司
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