1,2-Cyclohexanedione → HCID 11954760, compound

HRID 2358465Notes

Reaction equation

HRID 2358465 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@@H:3]([NH2:10])[C@H:2]1[OH:11].[C:12]1(=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=O>>[CH2:15]1[CH2:14][C@:13]2([O:11][C@H:2]3[CH2:1][C:9]4[C:4]([C@H:3]3[NH:10]2)=[CH:5][CH:6]=[CH:7][CH:8]=4)[C@@:12]2([O:19][C@H:2]3[CH2:1][C:9]4[C:4]([C@H:3]3[NH:10]2)=[CH:5][CH:6]=[CH:7][CH:8]=4)[CH2:17][CH2:16]1

Participants

3

Reactant 2

HCID 130061,2-CyclohexanedioneHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanol

Product 1

HCID 11954760HCID 11954760, compoundYield 90%

Procedure

For example, employing (1R,2S)-cis-1-amino-2-indanol in the acid-promoted reaction with 1,2-cyclohexanedione, bisoxazolidine 1 was obtained in 90% yield and 99% de (FIG. 1B). It was shown that compound 1 was produced with excellent diastereoselectivity and exclusive formation of the (S,S)—N,O-diketal by crystallographic analysis: careful evaporation of a solution of 1 in chloroform gave the single crystal suitable for crystallographic analysis (CDCC602445). (Crystal structure data: C24H26N2O2, monoclinic, space group P21, a=16.9199(16) Å, b=5.5487(5) Å, c=23.585(2) Å, α=90.00°, β=108.5190(10)°, γ=90.00°, V=2099.6(3) Å3, Z=4, ρcalcd=1.367 g cm−3, T=173 K.) It was shown that the ligand possesses a C2-symmetric structure and an averaged separation of 2.35 Å between the nitrogen and oxygen atoms which facilitates bidentate binding to metal ions and organometallic compounds (FIG. 1C). It was envisioned that 1, as well as other bisoxazolidines, would be useful for a variety of asymmetric reactions.

Sources & evidence

ORD record
ord-2aee01e5dc5a4b7ab5540e08f5ef4f45
Source dataset
uspto-grants-2010_07
Patent number
US07763734B2

Reaction notes

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