Convenient synthesis of a new class of chiral hydroxymethyl-dihydrooxazole ligands and their application in asymmetric addition of diethylzinc to aromatic aldehydes

Article abstract of DOI:10.1134/S1070428006040105

A number of chiral hydroxymethyl-substituted dihydrooxazoles were synthesized from D- or L-mandelic acid and amino alcohols. The chiral ligands thus obtained were tested as catalyst in the asymmetric addition of diethylzinc to aromatic aldehydes, and the

Full text of DOI:10.1134/S1070428006040105

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ZDVꢂKHDWHGꢂXQGHUꢂUHIOX[ꢂLQꢂDꢂIODVNꢂHTXLSSHGꢂZLWKꢂꢂ ꢃꢅꢌꢈꢋꢄꢂꢃꢅꢌꢈꢋꢄꢂ ꢃꢅꢉꢈꢅꢄꢂ ꢃꢎꢀꢈꢃꢄꢂ ꢃꢁꢃꢈꢌꢄꢂ ꢃꢏꢀꢈꢀꢄꢂ ꢃꢏꢉꢈꢉꢈꢂ ,5ꢂ
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ꢇ6ꢈꢁ>ꢇꢉ6ꢈꢁꢉꢁ%HQ]\OꢁꢉꢃꢊꢁGLK\GURR[D]ROꢁꢋꢁ\O@ꢁ
ꢇSKHQ\OꢈPHWK\OꢀDFHWDWHꢀꢇ,,Gꢈꢆꢂ<LHOGꢂꢌꢆꢈꢅ*ꢄꢂ> @ ꢂ ꢂ
ꢃꢌꢈꢋꢂꢐFꢂ ꢂꢅꢈꢆꢄꢂ(W2+ꢑꢈꢂ +ꢂ105ꢂVSHFWUXPꢄꢂ ꢄꢂSSPꢓꢂꢂ
ꢅꢈꢃꢌꢂVꢂꢐVꢄꢂꢎ+ꢄꢂ&+ &2ꢑꢄꢂꢅꢈꢏꢅꢂGꢈGꢂꢐꢃ+ꢄꢂ2&+ ꢄꢂ-ꢂ ꢂꢃꢏꢈꢌꢄꢂ
ꢇ6ꢈꢁ>ꢇꢉ6ꢈꢁꢉꢁ0HWK\OꢁꢉꢃꢊꢁGLK\GURR[D]ROꢁꢋꢁ\O@ꢁ
ꢇSKHQ\OꢈPHWK\Oꢀ DFHWDWHꢀ ꢇ,,Dꢈꢆꢂ<LHOGꢂꢌꢏꢈꢎ*ꢄꢂ> @ ꢂ ꢂꢂ ꢌꢈꢁꢂ +]ꢑꢄꢂ ꢎꢈꢆꢀꢂ Gꢂ ꢐꢃ+ꢄꢂ 3K&+ ꢄꢂ -ꢂ ꢀꢈꢅꢂ +] ꢑꢄꢂ ꢎꢈꢆꢉꢂ Gꢂ ꢐꢃ+ꢄꢂ
±ꢅꢃꢈꢌꢂ ꢐFꢂ ꢂ ꢅꢈꢌꢄꢂ (W2+ꢑꢈꢂ +ꢂ 105ꢂ VSHFWUXPꢄꢂ ꢄꢂ SSPꢓꢂ 3K&+ ꢄꢂ-ꢂ ꢂꢀꢈꢅꢂ+]ꢑꢄꢂꢁꢈꢆꢅꢂGꢈGꢂꢐꢃ+ꢄꢂ2&+ ꢄꢂ-ꢂ ꢂꢋꢈꢆꢄꢂꢃꢁꢈꢆꢂ
ꢃꢈꢅꢀꢂGꢂꢐꢎ+ꢄꢂ&+ ꢄꢂ-ꢂ ꢂꢏꢈꢏꢂ+]ꢑꢄꢂꢅꢈꢃꢋꢂVꢂꢐꢎ+ꢄꢂ&+ &2ꢑꢄꢂ +]ꢑꢄꢂꢁꢈꢃꢁꢂWꢂꢐꢃ+ꢄꢂ2&+ ꢄ -ꢂ ꢂꢉꢂ+]ꢑꢄꢂꢁꢈꢁꢅ±ꢁꢈꢁꢀꢂPꢂꢐꢃ+ꢄꢂ
ꢎꢈꢌꢀꢂ Wꢂ ꢐꢃ+ꢄꢂ 2&+ ꢄꢂ -ꢂ ꢂ ꢋꢈꢌꢂ +] ꢑꢄꢂ ꢁꢈꢅꢃ±ꢁꢈꢅꢀꢂ Pꢂ ꢐꢃ+ꢄꢂ 1&+ꢑꢄꢂꢏꢈꢅꢋꢂVꢂꢐꢃ+ꢄꢂ2&+ꢑꢄꢂꢋꢈꢃꢁ±ꢋꢈꢁꢏꢂPꢂꢐꢃꢆ+ꢄꢂ+ ꢑꢈꢂ
1&+ꢑꢄꢂꢎꢈꢌꢀꢂWꢂꢐꢃ+ꢄꢂ2&+ ꢄꢂ-ꢂ ꢂꢉꢈꢅꢂ+]ꢑꢄꢂꢏꢈꢅꢌꢂVꢂꢐꢃ+ꢄꢂ
2&+ꢑꢄꢂ ꢋꢈꢅꢏ±ꢋꢈꢁꢆꢂ Pꢂ ꢐꢅ+ꢄꢂ + ꢑꢄꢂ ꢋꢈꢁꢋ±ꢋꢈꢁꢉꢂ Pꢂ ꢐꢅ+ꢄꢂ ꢋꢅꢈꢎꢄꢂꢃꢅꢏꢈꢀꢄꢂꢃꢅꢋꢈꢀꢄꢂꢃꢅꢌꢈꢀꢄꢂꢃꢅꢌꢈꢋꢄꢂꢃꢅꢉꢈꢆꢄꢂꢃꢅꢉꢈꢅꢄꢂꢃꢎꢀꢈꢃꢄꢂ
ꢑꢈꢂ &ꢂ105ꢂVSHFWUXPꢄꢂ ꢄꢂSSPꢓꢂꢅꢆꢈꢉꢄꢂꢅꢃꢈꢅꢄꢂꢏꢃꢈꢏꢄꢂ ꢃꢎꢋꢈꢀꢄꢂꢃꢏꢁꢈꢀꢄꢂꢃꢏꢉꢈꢌꢈꢂ,5ꢂVSHFWUXPꢂꢐILOPꢑꢄꢂ ꢄꢂFP ꢓꢂꢎꢆꢏꢁꢄꢂ
&ꢂ 105ꢂ VSHFWUXPꢄꢂ ꢄꢂ SSPꢓꢂ ꢅꢆꢈꢉꢄꢂ ꢁꢃꢈꢎꢄꢂ ꢏꢋꢈꢅꢄꢂ ꢋꢆꢈꢌꢄꢂ
+
ꢋꢆꢈꢌꢄꢂꢋꢁꢈꢀꢄꢂꢃꢅꢋꢈꢏꢄꢂꢃꢅꢌꢈꢏꢄꢂꢃꢅꢉꢈꢆꢄꢂꢃꢎꢀꢈꢎꢄꢂꢃꢏꢎꢈꢌꢄꢂꢃꢏꢉꢈꢌꢈꢂ,5ꢂ ꢎꢆꢎꢆꢄꢂꢅꢉꢎꢆꢄꢂꢃꢋꢁꢏꢄꢂꢃꢏꢋꢅꢄꢂꢃꢅꢅꢉꢄꢂꢃꢆꢁꢁꢄꢂꢋꢉꢃꢄꢂꢋꢏꢃꢈꢂ)RXQGꢄꢂ
VSHFWUXPꢂꢐILOPꢑꢄꢂ ꢄꢂFP ꢓꢂꢎꢆꢎꢀꢄꢂꢅꢉꢏꢉꢄꢂꢃꢋꢁꢏꢄꢂꢃꢏꢋꢏꢄꢂꢃꢅꢆꢎꢄꢂ *ꢓꢂ&ꢂꢋꢎꢈꢋꢃꢍꢂ+ꢂꢏꢈꢃꢅꢍꢂ1ꢂꢁꢈꢁꢋꢈꢂ& + 12 ꢈꢂ&DOFXODWHGꢄꢂ
ꢃꢆꢁꢏꢄꢂꢋꢉꢅꢄꢂꢋꢏꢃꢈꢂ)RXQGꢄꢂ*ꢓꢂ&ꢂꢏꢏꢈꢌꢉꢍꢂ+ꢂꢏꢈꢁꢀꢍꢂ1ꢂꢀꢈꢉꢋꢈꢂ
& + 12 ꢈꢂ&DOFXODWHGꢄꢂ*ꢓꢂ&ꢂꢏꢏꢈꢉꢁꢍꢂ+ꢂꢏꢈꢁꢌꢍꢂ1ꢂꢏꢈꢆꢆꢈꢂꢂ
*ꢓꢂ&ꢂꢋꢎꢈꢋꢋꢍꢂ+ꢂꢏꢈꢃꢉꢍꢂ1ꢂꢁꢈꢀꢎꢈꢂ
ꢇ6ꢈꢁ>ꢇꢉ6ꢈꢁꢉꢁ,VRSURS\OꢁꢉꢃꢊꢁGLK\GURR[D]ROꢁꢋꢁ\O@ꢁ
ꢇSKHQ\OꢈPHWK\Oꢀ DFHWDWHꢀ ꢇ,,Hꢈꢆꢂ<LHOGꢂꢋꢉꢈꢋ*ꢄꢂ> @ ꢂ ꢂ
ꢇ6ꢈꢁ>ꢇꢉ6ꢈꢁꢉꢁ,VREXW\OꢁꢉꢃꢊꢁGLK\GURR[D]ROꢁꢋꢁ\O@ꢁ
ꢇSKHQ\OꢈPHWK\OꢀDFHWDWHꢀꢇ,,Eꢈꢆꢂ<LHOGꢂꢋꢉꢈꢋ*ꢄꢂ> @ ꢂ ꢂ ꢁꢈꢏꢀꢂ ꢐFꢂ ꢂ ꢅꢈꢃꢄꢂ (W2+ꢑꢈꢂ +ꢂ 105ꢂ VSHFWUXPꢄꢂ ꢄꢂ SSPꢓꢂꢂ
ꢏꢈꢏꢌꢂꢐFꢂ ꢂꢀꢈꢌꢄꢂ(W2+ꢑꢈꢂ +ꢂ105ꢂVSHFWUXPꢄꢂ ꢄꢂSSPꢓꢂ ꢆꢈꢌꢅꢂGꢂꢐꢎ+ꢄꢂ&+ ꢄꢂ-ꢂ ꢂꢏꢈꢌꢂ+]ꢑꢄꢂꢆꢈꢌꢉꢂGꢂꢐꢎ+ꢄꢂ&+ ꢄꢂ-ꢂ ꢂꢂ
ꢆꢈꢉꢃ±ꢆꢈꢉꢀꢂPꢂꢐꢏ+ꢄꢂ&+ ꢑꢄꢂꢃꢈꢅꢀ±ꢃꢈꢎꢃꢂPꢂꢐꢃ+ꢄꢂ&+ ꢑꢄꢂꢃꢈꢀꢋ±
ꢏꢈꢌꢂ+]ꢑꢄꢂꢃꢈꢋꢁ±ꢃꢈꢋꢋꢂPꢂꢐꢃ+ꢄꢂ&+ꢑꢄꢂꢅꢈꢃꢋꢂVꢂꢐꢎ+ꢄꢂ&+ &2ꢑꢄꢂ
ꢃꢈꢏꢀꢂPꢂꢐꢃ+ꢄꢂ&+ ꢑꢄꢂꢃꢈꢏꢉ±ꢃꢈꢋꢀꢂPꢂꢐꢃ+ꢄꢂ&+ꢑꢄꢂꢅꢈꢃꢉꢂVꢂꢐꢎ+ꢄꢂ ꢎꢈꢉꢋ±ꢁꢈꢆꢃꢂPꢂꢐꢃ+ꢄꢂ1&+ꢑꢄꢂꢁꢈꢆꢅꢂWꢂꢐꢃ+ꢄꢂ2&+ ꢄꢂ-ꢂ ꢂꢂ
&+ &2ꢑꢄꢂꢎꢈꢌꢉ±ꢎꢈꢉꢎꢂPꢂꢐꢃ+ꢄꢂ2&+ ꢑꢄꢂꢁꢈꢃꢌ±ꢁꢈꢅꢃꢂPꢂꢐꢃ+ꢄꢂ ꢌꢈꢎꢂ+]ꢑꢄꢂꢁꢈꢃꢉꢂWꢂꢐꢃ+ꢄꢂ2&+ ꢄꢂ-ꢂ ꢂꢌꢈꢎꢂ+]ꢑꢄꢂꢏꢈꢅꢌꢂVꢂꢐꢃ+ꢄꢂ
1&+ꢑꢄꢂꢁꢈꢎꢆ±ꢁꢈꢎꢀꢂPꢂꢐꢃ+ꢄꢂ2&+ ꢑꢄꢂꢏꢈꢅꢉꢂVꢂꢐꢃ+ꢄꢂ2&+ꢄꢂ-ꢂ ꢂ 2&+ꢑꢄꢂꢋꢈꢅꢏ±ꢋꢈꢀꢆꢂPꢂꢐꢀ+ꢄꢂ+ ꢑꢈꢂ &ꢂ105ꢂVSHFWUXPꢄꢂ
ꢅꢈꢏꢂ+]ꢑꢄꢂꢋꢈꢅꢉ±ꢋꢈꢀꢃꢂPꢂꢐꢀ+ꢄꢂ+ ꢑꢈꢂ &ꢂ105ꢂVSHFWUXPꢄꢂ
ꢄꢂSSPꢓ ꢅꢆꢈꢉꢄꢂꢅꢅꢈꢀꢄꢂꢅꢅꢈꢌꢄꢂꢅꢀꢈꢅꢄꢂꢁꢀꢈꢃꢄꢂꢏꢁꢈꢏꢄꢂꢋꢆꢈꢌꢄꢂꢋꢎꢈꢏꢄꢂ ꢃꢅꢌꢈꢏꢄꢂꢃꢅꢉꢈꢆꢄꢂꢃꢎꢀꢈꢅꢄꢂꢃꢏꢎꢈꢋꢄꢂꢃꢏꢉꢈꢌꢈꢂ,5ꢂVSHFWUXPꢂꢐILOPꢑꢄꢂ
ꢃꢅꢋꢈꢀꢄꢂꢃꢅꢌꢈꢏꢄꢂꢃꢅꢉꢈꢆꢄꢂꢃꢎꢀꢈꢅꢄꢂꢃꢏꢎꢈꢋꢄꢂꢃꢏꢉꢈꢋꢈꢂ,5ꢂVSHFWUXPꢂ ꢄꢂFP ꢓꢂꢎꢆꢎꢏꢄꢂꢅꢉꢏꢁꢄꢂꢃꢋꢁꢋꢄꢂꢃꢏꢋꢌꢄꢂꢃꢆꢁꢎꢄꢂꢋꢉꢁꢈꢂ)RXQGꢄꢂ*ꢓꢂ
ꢐILOPꢑꢄꢂ ꢄꢂFP ꢓ ꢎꢎꢁꢎꢄꢂꢅꢉꢀꢋꢄꢂꢃꢋꢁꢋꢄꢂꢃꢏꢋꢎꢄꢂꢃꢅꢅꢉꢄꢂꢃꢆꢁꢏꢄꢂ &ꢂꢏꢌꢈꢉꢆꢍꢂ+ꢂꢋꢈꢎꢃꢍꢂ1ꢂꢀꢈꢎꢃꢈꢂ& + 12 ꢈꢂ&DOFXODWHGꢄꢂ*ꢓꢂꢂ
ꢄꢂSSPꢓꢂꢃꢋꢈꢌꢄꢂꢃꢌꢈꢁꢄꢂꢅꢆꢈꢉꢄꢂꢎꢅꢈꢎꢄꢂꢋꢆꢈꢏꢄꢂꢋꢆꢈꢉꢄꢂꢋꢃꢈꢌꢄꢂꢃꢅꢋꢈꢀꢄꢂ
ꢋꢎꢁꢈꢂ)RXQGꢄꢂ*ꢓꢂ&ꢂꢏꢉꢈꢋꢋꢍꢂ+ꢂꢋꢈꢋꢆꢍꢂ1ꢂꢀꢈꢆꢌꢈꢂ& + 12 ꢈꢂ
&DOFXODWHGꢄꢂ*ꢓꢂ&ꢂꢏꢉꢈꢋꢉꢍꢂ+ꢂꢋꢈꢏꢉꢍꢂ1ꢂꢀꢈꢆꢉꢈꢂꢂ
&ꢂꢏꢌꢈꢉꢁꢍꢂ+ꢂꢋꢈꢎꢎꢍꢂ1ꢂꢀꢈꢎꢏꢈꢂꢂ
ꢇ6ꢈꢁ>ꢇꢉ6ꢈꢁꢉꢁWHUWꢁ%XW\OꢁꢉꢃꢊꢁGLK\GURR[D]ROꢁꢋꢁ\O@ꢁ
ꢇSKHQ\OꢈPHWK\OꢀDFHWDWHꢀꢇ,,Iꢈꢆꢂ<LHOGꢂꢏꢀꢈꢅ*ꢄꢂ> @ ꢂ ꢂꢂ
ꢇ5ꢈꢁꢇ3KHQ\Oꢈ>ꢇꢉ5ꢈꢁꢉꢁSKHQ\OꢁꢉꢃꢊꢁGLK\GURR[D]ROꢁꢋꢁ
\O@PHWK\OꢀDFHWDWHꢀ ꢇ,,Fꢈꢆꢂ<LHOGꢂꢌꢆ*ꢄꢂ> @ ꢂ ꢂꢏꢈꢏꢌꢂꢐFꢂ ꢂ ±ꢆꢈꢀꢂ ꢐFꢂ ꢂ ꢁꢈꢅꢄꢂ (W2+ꢑꢈꢂ +ꢂ 105ꢂ VSHFWUXPꢄꢂ ꢄꢂ SSPꢓꢂꢂ
ꢀꢈꢌꢄꢂ (W2+ꢑꢈꢂ +ꢂ 105ꢂ VSHFWUXPꢄꢂ ꢄꢂ SSPꢓꢂ ꢅꢈꢅꢆꢂ Vꢂ ꢐꢎ+ꢄꢂ ꢆꢈꢌꢀꢂVꢂ>ꢉ+ꢄꢂꢐ&+ ꢑ @ꢄꢂꢅꢈꢃꢉꢂVꢂꢐꢎ+ꢄꢂ&+ &2ꢑꢄꢂꢎꢈꢉꢆ±ꢎꢈꢉꢅꢂPꢂ
&+ &2ꢑꢄꢂꢁꢈꢃꢅ±ꢁꢈꢃꢏꢂPꢂꢐꢃ+ꢄꢂ2&+ ꢑꢄꢂꢁꢈꢀꢌ±ꢁꢈꢏꢎꢂPꢂꢐꢃ+ꢄꢂ ꢐꢃ+ꢄꢂ1&+ꢑꢄꢂꢁꢈꢃꢁ±ꢁꢈꢃꢋꢂPꢂꢐꢅ+ꢄꢂ2&+ ꢑꢄꢂꢏꢈꢅꢌꢂVꢂꢐꢃ+ꢄꢂꢂ
5866,$1ꢂꢂ-2851$/ꢂꢂ2)ꢂꢂ25*$1,&ꢂꢂ&+(0,675<ꢂꢂꢂ9ROꢈꢂꢂꢁꢅꢂꢂꢂ1Rꢈꢂꢂꢁꢂꢂꢂꢅꢆꢆꢏꢂ

=+,ꢇ7,1*ꢂ/,ꢂꢂHWꢂDOꢈꢂ
ꢀꢁꢌꢂ
2&+ꢑꢄꢂꢋꢈꢎꢏ±ꢋꢈꢀꢆꢂPꢂꢐꢀ+ꢄꢂ+ ꢑꢈꢂ &ꢂ105ꢂVSHFWUXPꢄꢂ ꢅꢉꢆꢋꢄꢂ ꢃꢏꢏꢎꢄꢂ ꢃꢃꢋꢋꢄꢂ ꢋꢏꢃꢈꢂ )RXQGꢄꢂ *ꢓꢂ &ꢂ ꢋꢅꢈꢆꢃꢍꢂ +ꢂ ꢌꢈꢃꢌꢍꢂꢂ
ꢄꢂSSPꢓꢂꢅꢆꢈꢉꢄꢂꢅꢀꢈꢏꢄꢂꢎꢎꢈꢉꢄꢂꢏꢉꢈꢀꢄꢂꢋꢃꢈꢆꢄꢂꢋꢀꢈꢀꢄꢂꢃꢅꢋꢈꢀꢄꢂ 1ꢂꢀꢈꢉꢀꢈꢂ& + 12 ꢈꢂ&DOFXODWHGꢄꢂ*ꢓꢂ&ꢂꢋꢅꢈꢆꢋꢍꢂ+ꢂꢌꢈꢅꢃꢍꢂꢂ
ꢃꢅꢌꢈꢏꢄꢂꢃꢅꢌꢈꢋꢄꢂꢃꢅꢉꢈꢆꢄꢂꢃꢎꢀꢈꢅꢄꢂꢃꢏꢎꢈꢋꢄꢂꢃꢏꢉꢈꢌꢈꢂ,5ꢂVSHFWUXPꢂ 1ꢂꢏꢈꢆꢆꢈꢂꢂ
ꢐILOPꢑꢄꢂ ꢄꢂ FP ꢓꢂ ꢎꢆꢎꢀꢄꢂ ꢅꢉꢀꢀꢄꢂ ꢃꢋꢀꢆꢄꢂ ꢃꢏꢋꢌꢄꢂ ꢃꢆꢁꢏꢄꢂ ꢏꢉꢌꢈꢂ
)RXQGꢄꢂ*ꢓꢂ&ꢂꢏꢉꢈꢋꢏꢍꢂ+ꢂꢋꢈꢏꢉꢍꢂ1ꢂꢀꢈꢆꢌꢈꢂ& + 12 ꢈꢂ&DOꢇ
FXODWHGꢄꢂ*ꢓꢂ&ꢂꢏꢉꢈꢋꢉꢍꢂ+ꢂꢋꢈꢏꢉꢍꢂ1ꢂꢀꢈꢆꢉꢈꢂꢂ
ꢇ5ꢈꢁꢇ3KHQ\Oꢈ>ꢇꢉ5ꢈꢁꢉꢁSKHQ\OꢁꢉꢃꢊꢁGLK\GURR[D]ROꢁꢋꢁ
\O@PHWKDQROꢀ ꢇ,Fꢈꢆꢂ<LHOGꢂꢌꢋ*ꢄꢂPSꢂꢃꢃꢆ±ꢃꢃꢅƒ&ꢄꢂ> @ ꢂ ꢂ
ꢅꢃꢈꢅꢉꢂꢐFꢂ ꢂꢃꢈꢆꢄꢂ&+ &O ꢑꢈꢂ +ꢂ105ꢂVSHFWUXPꢄꢂ ꢄꢂSSPꢓꢂ
ꢁꢈꢃꢉꢂVꢂꢐꢃ+ꢄꢂ2+ꢑꢄꢂꢁꢈꢅꢃ±ꢁꢈꢅꢏꢂPꢂꢐꢃ+ꢄꢂ2&+ ꢑꢄꢂꢁꢈꢏꢎ±ꢂ
ꢁꢈꢏꢌꢂPꢂꢐꢃ+ꢄꢂ2&+ ꢑꢄꢂꢀꢈꢃꢏ±ꢀꢈꢅꢆꢂWꢂꢐꢃ+ꢄꢂ1&+ꢄꢂ-ꢂ ꢂꢂ
ꢇ5ꢈꢁ>ꢇꢉ6ꢈꢁꢉꢁ,VRSURS\OꢁꢉꢃꢊꢁGLK\GURR[D]ROꢁꢋꢁ\O@ꢁ
ꢇSKHQ\OꢈPHWK\Oꢀ DFHWDWHꢀ ꢇ,,Jꢈꢆꢂ<LHOGꢂꢌꢎꢈꢋ*ꢄꢂ> @ ꢂ ꢂꢂ
±ꢉꢁꢈꢀꢂꢐFꢂ ꢂꢅꢄꢂ(W2+ꢑꢈꢂ +ꢂ105ꢂVSHFWUXPꢄꢂ ꢄꢂSSPꢓꢂꢆꢈꢌꢅꢂGꢂ ꢌꢈꢁꢂ+]ꢑꢄꢂꢀꢈꢅꢉꢂVꢂꢐꢃ+ꢄꢂ2&+ꢑꢄꢂꢋꢈꢅꢁ±ꢋꢈꢁꢉꢂPꢂꢐꢃꢆ+ꢄꢂ+ ꢑꢈꢂ
ꢐꢎ+ꢄꢂ&+ ꢄꢂ-ꢂ ꢂꢏꢈꢌꢂ+]ꢑꢄꢂꢆꢈꢉꢅꢂGꢂꢐꢎ+ꢄꢂ&+ ꢄꢂ-ꢂ ꢂꢏꢈꢌꢂ+]ꢑꢄꢂ
ꢃꢈꢌꢁ±ꢃꢈꢌꢀꢂPꢂꢐꢃ+ꢄꢂ&+ꢑꢄꢂꢅꢈꢃꢋꢂVꢂꢐꢎ+ꢄꢂ&+ &2ꢑꢄꢂꢎꢈꢉꢁ±
&ꢂ105ꢂVSHFWUXPꢄꢂ ꢄꢂSSPꢓꢂꢏꢌꢈꢋꢄꢂꢏꢉꢈꢏꢄꢂꢋꢏꢈꢎꢄꢂꢃꢅꢏꢈꢀꢄꢂ
ꢃꢅꢏꢈꢏꢄꢂꢃꢅꢏꢈꢏꢄꢂꢃꢅꢋꢈꢌꢄꢂꢃꢅꢌꢈꢁꢄꢂꢃꢅꢌꢈꢀꢄꢂꢃꢅꢌꢈꢌꢄꢂꢃꢎꢉꢈꢆꢄꢂꢃꢁꢃꢈꢀꢄꢂ
ꢎꢈꢉꢉꢂ Pꢂ ꢐꢅ+ꢄꢂ 2&+ ꢑꢄꢂ ꢁꢈꢅꢁꢂ Wꢂ ꢐꢃ+ꢄꢂ 1&+ꢄꢂ -ꢂ ꢂ ꢌꢈꢆꢂ +] ꢑꢄꢂ ꢃꢏꢌꢈꢌꢈꢂ,5ꢂVSHFWUXPꢂꢐ.%Uꢑꢄꢂ ꢄꢂFP ꢓꢂꢎꢁꢃꢆꢄꢂꢅꢉꢆꢌꢄꢂꢃꢏꢁꢁꢄꢂ
ꢏꢈꢅꢉꢂVꢂꢐꢃ+ꢄꢂ2&+ꢑꢄꢂꢋꢈꢎꢀ±ꢋꢈꢀꢃꢂPꢂꢐꢀ+ꢄꢂ+ ꢑꢈꢂ &ꢂ105ꢂ ꢃꢁꢀꢀꢄꢂ ꢃꢃꢋꢋꢄꢂ ꢃꢆꢌꢆꢄꢂ ꢋꢏꢆꢈꢂ )RXQGꢄꢂ *ꢓꢂ &ꢂ ꢋꢀꢈꢌꢎꢍꢂ +ꢂ ꢀꢈꢉꢏꢍꢂꢂ
VSHFWUXPꢄꢂ ꢄꢂSSPꢓꢂꢃꢋꢈꢌꢄꢂꢃꢌꢈꢁꢄꢂꢅꢆꢈꢉꢄꢂꢎꢅꢈꢎꢄꢂꢋꢆꢈꢏꢄꢂꢋꢆꢈꢉꢄꢂ 1ꢂꢀꢈꢀꢃꢈꢂ& + 12 ꢈꢂ&DOFXODWHGꢄꢂ*ꢓꢂ&ꢂꢋꢀꢈꢌꢋꢍꢂ+ꢂꢀꢈꢉꢋꢍꢂꢂ
ꢋꢃꢈꢌꢄꢂꢃꢅꢋꢈꢀꢄꢂꢃꢅꢌꢈꢏꢄꢂꢃꢅꢉꢈꢆꢄꢂꢃꢎꢀꢈꢅꢄꢂꢃꢏꢎꢈꢋꢄꢂꢃꢏꢉꢈꢌꢈꢂ,5ꢂVSHFꢇ
WUXPꢂꢐILOPꢑꢄꢂ ꢄꢂFP ꢓꢂꢎꢆꢎꢏꢄꢂꢅꢉꢏꢃꢄꢂꢃꢋꢁꢋꢄꢂꢃꢏꢋꢌꢄꢂꢃꢆꢁꢎꢄꢂ
ꢋꢉꢁꢈꢂ)RXQGꢄꢂ*ꢓꢂ&ꢂꢏꢌꢈꢉꢃꢍꢂ+ꢂꢋꢈꢎꢎꢍꢂ1ꢂꢀꢈꢎꢁꢈꢂ& + 12 ꢈꢂ
&DOFXODWHGꢄꢂ*ꢓꢂ&ꢂꢏꢌꢈꢉꢁꢍꢂ+ꢂꢋꢈꢎꢎꢍꢂ1ꢂꢀꢈꢎꢏꢈꢂꢂ
1ꢂꢀꢈꢀꢎꢈꢂꢂ
ꢇ6ꢈꢁ>ꢇꢉ6ꢈꢁꢉꢁ%HQ]\OꢁꢉꢃꢊꢁGLK\GURR[D]ROꢁꢋꢁ\O@ꢁ
ꢇSKHQ\OꢈPHWKDQROꢀꢇ,Gꢈꢆꢂ<LHOGꢂꢉꢅ*ꢄꢂPSꢂꢃꢆꢋ±ꢃꢆꢌꢈꢀƒ&ꢄꢂ
> @ ꢂ ꢂ±ꢁꢌꢈꢎꢃꢂꢐFꢂ ꢂꢃꢈꢆꢄꢂ(W2+ꢑꢈꢂ +ꢂ105ꢂVSHFWUXPꢄꢂ ꢄꢂ
SSPꢓꢂꢅꢈꢏꢉꢂGꢈGꢂꢐꢃ+ꢄꢂ2&+ ꢄꢂ-ꢂ ꢂꢃꢏꢈꢆꢄꢂꢌꢈꢆꢂ+]ꢑꢄꢂꢎꢈꢆꢏꢂGꢂ
*HQHUDOꢀSURFHGXUHꢀIRUꢀWKHꢀSUHSDUDWLRQꢀRIꢀGLK\ꢁ
GURR[D]ROHVꢀ,D±,Jꢆꢂ&RPSRXQGꢂ,,D±,,JꢄꢂꢀꢂPPROꢄꢂZDVꢂ ꢐꢃ+ꢄꢂ3K&+ ꢄꢂ-ꢂ ꢂꢀꢈꢏꢂ+]ꢑꢄꢂꢎꢈꢆꢉꢂGꢂꢐꢃ+ꢄꢂ3K&+ ꢄꢂ-ꢂ ꢂꢂ
GLVVROYHGꢂLQꢂꢃꢀꢂPOꢂRIꢂHWKDQROꢄꢂWKHꢂVROXWLRQꢂZDVꢂFRROHGꢂ ꢀꢈꢏꢂ +]ꢑꢄꢂꢎꢈꢌꢎꢂ Vꢂꢐꢃ+ꢄꢂ 2+ꢑꢄꢂꢁꢈꢆꢌꢂWꢂ ꢐꢃ+ꢄꢂ 2&+ ꢄꢂ -ꢂ ꢂꢂ
WRꢂꢆƒ&ꢄꢂDQGꢂꢃꢆꢂPOꢂRIꢂꢅꢆ*ꢂDTXHRXVꢂVRGLXPꢂK\GUR[LGHꢂ ꢌꢈꢁꢂ+]ꢑꢄꢂꢁꢈꢅꢃꢂWꢂꢐꢃ+ꢄꢂ2&+ ꢄꢂ-ꢂ ꢂꢌꢈꢁꢂ+]ꢑꢄꢂꢁꢈꢅꢏ±ꢁꢈꢁꢆꢂPꢂ
ZDVꢂDGGHGꢈꢂ7KHꢂPL[WXUHꢂZDVꢂVWLUUHGꢂIRUꢂꢅꢂKꢂDWꢂꢆƒ&ꢂDQGꢂ ꢐꢃ+ꢄꢂ1&+ꢑꢄꢂꢀꢈꢅꢏꢂVꢂꢐꢃ+ꢄꢂ2&+ꢑꢄꢂꢋꢈꢃꢌ±ꢋꢈꢁꢅꢂPꢂꢐꢃꢆ+ꢄꢂ
WUHDWHGꢂZLWKꢂGLHWK\OꢂHWKHUꢂꢐꢎîꢃꢆꢂPOꢑꢄꢂWKHꢂRUJDQLFꢂ
+
ꢑꢈꢂ &ꢂ105ꢂVSHFWUXPꢄꢂ ꢄꢂSSPꢓꢂꢁꢆꢈꢌꢄꢂꢏꢀꢈꢌꢄꢂꢏꢉꢈꢃꢄꢂ
H[WUDFWVꢂZHUHꢂFRPELQHGꢄꢂGULHGꢂRYHUꢂDQK\GURXVꢂ1D 62 ꢄꢂ ꢋꢅꢈꢌꢄꢂꢃꢅꢀꢈꢉꢄꢂꢃꢅꢏꢈꢎꢄꢂꢃꢅꢋꢈꢋꢄꢂꢃꢅꢋꢈꢉꢄꢂꢃꢅꢌꢈꢅꢄꢂꢃꢅꢌꢈꢏꢄꢂꢃꢅꢌꢈꢉꢄꢂ
DQGꢂFRQFHQWUDWHGꢂXQGHUꢂUHGXFHGꢂSUHVVXUHꢄꢂDQGꢂWKHꢂ ꢃꢅꢉꢈꢅꢄꢂꢃꢎꢏꢈꢌꢄꢂꢃꢎꢋꢈꢃꢄꢂꢃꢏꢎꢈꢀꢈꢂ,5ꢂVSHFWUXPꢂꢐ.%Uꢑꢄꢂ ꢄꢂFP ꢓꢂ
UHVLGXHꢂꢐDꢂZKLWHꢂVROLGꢑꢂZDVꢂUHFU\VWDOOL]HGꢂIURPꢂGLHWK\Oꢂ ꢎꢎꢉꢋꢄꢂꢅꢉꢅꢎꢄꢂꢃꢏꢏꢋꢄꢂꢃꢁꢉꢅꢄꢂꢃꢃꢉꢃꢄꢂꢃꢆꢏꢌꢄꢂꢋꢎꢌꢈꢂ)RXQGꢄꢂ*ꢓꢂꢂ
HWKHU±KH[DQHꢈꢂ
&ꢂꢋꢏꢈꢎꢀꢍꢂ+ꢂꢏꢈꢁꢀꢍꢂ1ꢂꢀꢈꢅꢆꢈꢂ& + 12 ꢈꢂ&DOFXODWHGꢄꢂ*ꢓꢂ
&ꢂꢋꢏꢈꢎꢌꢍꢂ+ꢂꢏꢈꢁꢃꢍꢂ1ꢂꢀꢈꢅꢁꢈꢂꢂ
ꢇ6ꢈꢁ>ꢇꢉ6ꢈꢁꢉꢁ0HWK\OꢁꢉꢃꢊꢁGLK\GURR[D]ROꢁꢋꢁ\O@ꢁ
ꢇSKHQ\OꢈPHWKDQROꢀ ꢇ,Dꢈꢆꢂ<LHOGꢂꢌꢆ*ꢄꢂPSꢂꢉꢏ±ꢉꢌƒ&ꢄꢂꢂ
> @ ꢂ ꢂ±ꢏꢀꢈꢅꢀꢂꢐFꢂ ꢂꢃꢈꢅꢄꢂ(W2+ꢑꢈꢂ +ꢂ105ꢂVSHFWUXPꢄꢂ ꢄꢂ
ꢇ6ꢈꢁ>ꢇꢉ6ꢈꢁꢉꢁ,VRSURS\OꢁꢉꢃꢊꢁGLK\GURR[D]ROꢁꢋꢁ\O@ꢁ
ꢇSKHQ\OꢈPHWKDQROꢀ ꢇ,Hꢈꢆꢂ <LHOGꢂ ꢌꢀ*ꢄꢂ PSꢂ ꢉꢁꢈꢀ±ꢉꢏƒ&ꢄꢂꢂ
SSPꢓꢂꢃꢈꢅꢏ±ꢃꢈꢅꢉꢂPꢂꢐꢎ+ꢄꢂ&+ ꢑꢄꢂꢎꢈꢌꢋ±ꢎꢈꢉꢅꢂPꢂꢐꢃ+ꢄꢂ > @ ꢂ ꢂ±ꢋꢎꢈꢀꢁꢂꢐFꢂ ꢂꢃꢈꢃꢄꢂ(W2+ꢑꢈꢂ +ꢂ105ꢂVSHFWUXPꢄꢂ ꢄꢂ
2&+ ꢑꢄꢂ ꢁꢈꢃꢎ±ꢁꢈꢃꢉꢂ Pꢂ ꢐꢃ+ꢄꢂ 1&+ꢑꢄꢂ ꢁꢈꢎꢁ±ꢁꢈꢁꢆꢂ Pꢂ ꢐꢃ+ꢄꢂ SSPꢓꢂꢆꢈꢌꢋꢂGꢂꢐꢎ+ꢄꢂ&+ ꢄꢂ-ꢂ ꢂꢏꢈꢌꢂ+]ꢑꢄꢂꢆꢈꢉꢏꢂGꢂꢐꢎ+ꢄꢂ&+ ꢄꢂꢂ
2&+ ꢑꢄꢂꢀꢈꢅꢉꢂVꢂꢐꢃ+ꢄꢂ2&+ꢑꢄꢂꢋꢈꢅꢏ±ꢋꢈꢁꢏꢂPꢂꢐꢀ+ꢄꢂ+ ꢑꢈꢂ -ꢂ ꢂꢏꢈꢌꢂ+]ꢑꢄꢂꢃꢈꢋꢃ±ꢃꢈꢋꢌꢂPꢂꢐꢃ+ꢄꢂ&+ꢑꢄꢂꢎꢈꢌꢁ±ꢎꢈꢉꢆꢂPꢂꢐꢃ+ꢄꢂ
&ꢂ 105ꢂ VSHFWUXPꢄꢂ ꢄꢂ SSPꢓꢂ ꢅꢃꢈꢅꢄꢂ ꢏꢆꢈꢌꢄꢂ ꢏꢉꢈꢋꢄꢂ ꢋꢀꢈꢀꢄꢂ 1&+ꢑꢄꢂꢎꢈꢉꢉꢂVꢂꢐꢃ+ꢄꢂ2+ꢂꢑꢄꢂꢁꢈꢆꢀꢂWꢂꢐꢃ+ꢄꢂ2&+ ꢄꢂ-ꢂ ꢂꢂ
ꢋꢀꢈꢏꢄꢂꢃꢅꢏꢈꢏꢄꢂꢃꢅꢌꢈꢎꢄꢂꢃꢅꢌꢈꢁꢄꢂꢃꢅꢌꢈꢀꢄꢂꢃꢎꢉꢈꢃꢄꢂꢃꢏꢌꢈꢎꢈꢂ,5ꢂVSHFꢇ
ꢌꢈꢎꢂ+]ꢑꢄꢂꢁꢈꢅꢀꢂWꢂꢐꢃ+ꢄꢂ2&+ ꢄꢂ-ꢂ ꢂꢌꢈꢎꢂ+]ꢑꢄꢂꢀꢈꢅꢉꢂVꢂꢐꢃ+ꢄꢂ
WUXPꢂꢐ.%Uꢑꢄꢂ ꢄꢂFP ꢓꢂꢎꢁꢀꢉꢄꢂꢅꢉꢋꢁꢄꢂꢃꢏꢋꢆꢄꢂꢃꢃꢌꢋꢄꢂꢃꢆꢏꢏꢄꢂ 2&+ꢑꢄꢂꢋꢈꢅꢀ±ꢋꢈꢁꢏꢂPꢂꢐꢀ+ꢄꢂ+ ꢑꢈꢂ &ꢂ105ꢂVSHFWUXPꢄꢂ
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ꢄꢂSSPꢓꢂꢃꢌꢈꢅꢄꢂꢃꢌꢈꢏꢄꢂꢎꢅꢈꢏꢄꢂꢏꢉꢈꢏꢄꢂꢋꢃꢈꢎꢄꢂꢋꢅꢈꢆꢄꢂꢃꢅꢏꢈꢏꢄꢂ
ꢃꢅꢌꢈꢎꢄꢂꢃꢅꢌꢈꢀꢄꢂꢃꢎꢉꢈꢅꢄꢂꢃꢏꢌꢈꢎꢈꢂ,5ꢂVSHFWUXPꢂꢐ.%Uꢑꢄꢂ ꢄꢂFP ꢓꢂ
ꢎꢁꢃꢏꢄꢂꢅꢉꢀꢉꢄꢂꢃꢏꢋꢆꢄꢂꢃꢏꢁꢎꢄꢂꢃꢅꢏꢁꢄꢂꢃꢃꢉꢎꢄꢂꢃꢆꢌꢋꢄꢂꢋꢁꢉꢈꢂ
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FXODWHGꢄꢂ*ꢓꢂ&ꢂꢋꢃꢈꢅꢃꢍꢂ+ꢂꢋꢈꢌꢃꢍꢂ1ꢂꢏꢈꢎꢉꢈꢂꢂ
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ꢇSKHQ\OꢈPHWKDQROꢀ ꢇ,Eꢈꢆꢂ <LHOGꢂ ꢉꢆ*ꢄꢂ PSꢂ ꢃꢆꢃ±ꢃꢆꢅƒ&ꢄꢂ
> @ ꢂ ꢂ±ꢋꢃꢈꢃꢋꢂꢐFꢂ ꢂꢃꢈꢅꢄꢂ(W2+ꢑꢈꢂ +ꢂ105ꢂVSHFWUXPꢄꢂ ꢄꢂ
SSPꢓꢂꢆꢈꢉꢃ±ꢆꢈꢉꢀꢂPꢂꢐꢏ+ꢄꢂ&+ ꢑꢄꢂꢃꢈꢅꢁꢂPꢂꢐꢃ+ꢄꢂ&+ ꢑꢄꢂꢃꢈꢀꢉ±
ꢃꢈꢏꢁꢂPꢂꢐꢃ+ꢄꢂ&+ ꢑꢄꢂꢃꢈꢋꢏ±ꢃꢈꢋꢋꢂPꢂꢐꢃ+ꢄꢂ&+ꢑꢄꢂꢎꢈꢉꢆ±ꢎꢈꢉꢀꢂPꢂ
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ꢇSKHQ\OꢈPHWKDQROꢀꢇ,Iꢈꢆꢂ<LHOGꢂꢌꢌ*ꢄꢂPSꢂꢃꢎꢅƒ&ꢄꢂ> @ ꢂ ꢂ
ꢐꢃ+ꢄꢂ2&+ ꢑꢄꢂꢁꢈꢃꢆ±ꢁꢈꢃꢁꢂPꢂꢐꢃ+ꢄꢂ1&+ꢑꢄꢂꢁꢈꢎꢁ±ꢁꢈꢎꢉꢂPꢂ ±ꢏꢌꢈꢀꢂꢐFꢂ ꢂꢃꢄꢂ(W2+ꢑꢈꢂ +ꢂ105ꢂVSHFWUXPꢄꢂ ꢄꢂSSPꢓꢂꢂ
ꢐꢃ+ꢄꢂ2&+ ꢑꢄꢂꢀꢈꢅꢏꢂGꢂꢐꢃ+ꢄꢂ2&+ꢄꢂ-ꢂ ꢂꢁꢈꢎꢂ+]ꢑꢄꢂꢋꢈꢅꢀ±ꢂ ꢆꢈꢉꢃꢂ Vꢂ >ꢉ+ꢄꢂ ꢐ&+ ꢑ @ꢄꢂ ꢎꢈꢋꢆꢂ Vꢂ ꢐꢃ+ꢄꢂ 2+ꢑꢄꢂ ꢎꢈꢌꢁꢂ GꢈGꢂ ꢐꢃ+ꢄꢂ
ꢋꢈꢁꢀꢂPꢂꢐꢀ+ꢄꢂ+ ꢑꢈꢂ &ꢂ105ꢂVSHFWUXPꢄꢂ ꢄꢂSSPꢓꢂꢅꢅꢈꢏꢄꢂ 1&+ꢄꢂ-ꢂ ꢂꢌꢈꢆꢄꢂꢃꢅꢂ+]ꢑꢄꢂꢁꢈꢃꢋ±ꢁꢈꢅꢃꢂPꢂꢐꢅ+ꢄꢂ2&+ ꢑꢄꢂꢀꢈꢅꢉꢂVꢂ
ꢅꢅꢈꢋꢄꢂꢅꢀꢈꢎꢄꢂꢁꢀꢈꢎꢄꢂꢏꢎꢈꢌꢄꢂꢏꢉꢈꢋꢄꢂꢋꢁꢈꢌꢄꢂꢃꢅꢏꢈꢏꢄꢂꢃꢅꢌꢈꢎꢄꢂꢃꢅꢌꢈꢀꢄꢂ ꢐꢃ+ꢄꢂ2&+ꢑꢄꢂꢋꢈꢎꢎ±ꢋꢈꢁꢋꢂPꢂꢐꢀ+ꢄꢂ+ ꢑꢈꢂ &ꢂ105ꢂVSHFꢇ
ꢃꢎꢉꢈꢃꢄꢂꢃꢏꢎꢈꢋꢄꢂꢃꢏꢌꢈꢁꢈꢂ,5ꢂVSHFWUXPꢂꢐ.%Uꢑꢄꢂ ꢄꢂFP ꢓꢂꢎꢁꢆꢃꢄꢂ WUXPꢄꢂ ꢄꢂSSPꢓꢂꢅꢀꢈꢋꢄꢂꢎꢎꢈꢏꢄꢂꢏꢉꢈꢏꢄꢂꢋꢆꢈꢏꢄꢂꢋꢁꢈꢌꢄꢂꢃꢅꢎꢈꢀꢄꢂ
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