One-pot diastereoselective synthesis of α-aminonitriles from aldehydes, chiral amines, and trimethylsilyl cyanide under solvent-free conditions

Article abstract of DOI:10.1134/S1070428006010088

Treatment of aliphatic and aromatic aldehydes with chiral amines and trimethylsilyl cyanide in the absence or in the presence of Lewis acids (including lithium perchlorate) under solvent-free conditions afforded the corresponding α-aminonitriles in good y

Full text of DOI:10.1134/S1070428006010088

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DPLQRꢉDFHWRQLWULOHꢁꢈ9,Kꢉꢂ>ꢃꢀ@ꢋꢂ,5ꢂVSHFWUXPꢂꢈ&+ &O ꢉꢅꢂ
ꢅꢂFP ꢑꢁꢍꢍꢆꢏꢋꢏꢂꢈ1+ꢉꢅꢂꢆꢆꢍꢆꢋꢐꢂꢈ&1ꢉꢋꢂ +ꢂ105ꢂVSHFWUXPꢂ
ꢈꢎꢇꢇꢂ0+]ꢅꢂ&'&O ꢉꢅꢂ ꢅꢂSSPꢑꢂꢃꢋꢀꢐꢂGꢂꢈꢍ+ꢅꢂ-ꢂ ꢂꢄꢋꢁꢂ+]ꢉꢅꢂ
ꢃꢋꢁꢍꢂGꢂꢈꢃ+ꢅꢂ-ꢂ ꢂꢃꢆꢋꢃꢂ+]ꢉꢅꢂꢀꢋꢆꢐꢂTꢂꢈꢃ+ꢅꢂ-ꢂ ꢂꢄꢋꢁꢂ+]ꢉꢅꢂꢂ
ꢀꢋꢍꢏꢂGꢂꢈꢃ+ꢅꢂ-ꢂ ꢂꢃꢆꢋꢃꢂ+]ꢉꢅꢂꢐꢋꢆꢆ±ꢐꢋꢄꢎꢂPꢂꢈꢏ+ꢉꢋꢂ
ꢂ
ꢂꢂꢎꢋꢂ &KDYDURWꢅꢂ0ꢋꢅꢂ%\UQHꢅꢂ-ꢋ-ꢋꢅꢂ&KDYDQWꢅꢂ3ꢋꢊ<ꢋꢅꢂDQGꢂ9DOOHHꢅꢂ<ꢋꢅꢂ
ꢂ
7HWUDKHGURQꢇ $V\PPHWU\ꢅꢂꢆꢇꢇꢃꢅꢂYROꢋꢂꢃꢆꢅꢂSꢋꢂꢃꢃꢀꢐꢋꢂꢂ
ꢂꢂꢄꢋꢂ 0RULꢅꢂ0ꢋꢅꢂ,PPDꢅꢂ+ꢋꢅꢂDQGꢂ1DNDLꢅꢂ7ꢋꢅꢂ 7HWUDKHGURQ /HWWꢋꢅꢂ
ꢃꢏꢏꢐꢅꢂYROꢋꢂꢍꢁꢅꢂSꢋꢂꢄꢆꢆꢏꢋꢂꢂ
ꢂꢂꢐꢋꢂ 6LJPDQꢅꢂ 0ꢋ6ꢋꢂ DQGꢂ -DFREVHQꢅꢂ (ꢋ1ꢋꢅꢂ -ꢈ $Pꢈ &KHPꢈ 6RFꢋꢅꢂ
ꢃꢏꢏꢁꢅꢂYROꢋꢂꢃꢆꢇꢅꢂSꢋꢂꢎꢍꢃꢎꢋꢂꢂ
ꢂꢂꢁꢋꢂ 9DFKDOꢅꢂ3ꢋꢂDQGꢂ-DFREVHQꢅꢂ(ꢋ1ꢋꢅꢂ-ꢈ $Pꢈ &KHPꢈ 6RFꢋꢅꢂꢆꢇꢇꢆꢅꢂ
YROꢋꢂꢃꢆꢀꢅꢂSꢋꢂꢃꢇꢋꢂꢂ
ꢂꢂꢏꢋꢂ 7DNDPXUDꢅꢂ 0ꢋꢅꢂ +DPDVKLPDꢅꢂ<ꢋꢅꢂ 8VXGDꢅꢂ +ꢋꢅꢂ .DQDLꢅꢂ 0ꢋꢅꢂ
ꢂ
ꢈ5ꢂ5ꢉꢀꢇꢀꢈꢇꢂꢊꢀ'LFKORURSKHQ\OꢉꢀꢇꢀꢈꢆꢀSKHQ\OHWK\Oꢀ
DPLQRꢉDFHWRQLWULOHꢁ ꢈ9,Lꢉꢂ>ꢃꢏ@ꢋꢂ,5ꢂVSHFWUXPꢂꢈ&+ &O ꢉꢅꢂ
ꢅꢂFP ꢑꢁꢍꢍꢍꢃꢋꢆꢂꢈ1+ꢉꢅꢂꢆꢆꢍꢎꢋꢆꢂꢈ&1ꢉꢋꢂ +ꢂ105ꢂVSHFWUXPꢂ
ꢈꢎꢇꢇꢂ0+]ꢅꢂ&'&O ꢉꢅꢂ ꢅꢂSSPꢑꢂꢃꢋꢀꢐꢂGꢂꢈꢍ+ꢅꢂ-ꢂ ꢂꢄꢋꢄꢂ+]ꢉꢅꢂ
ꢃꢋꢁꢀꢂGꢂꢈꢃ+ꢅꢂ-ꢂ ꢂꢃꢃꢋꢃꢂ+]ꢉꢅꢂꢀꢋꢆꢎꢂTꢂꢈꢃ+ꢅꢂ-ꢂ ꢂꢄꢋꢎꢂ+]ꢉꢅꢂꢂ
ꢀꢋꢄꢎꢂGꢂꢈꢃ+ꢅꢂ-ꢂ ꢂꢃꢃꢋꢀꢂ+]ꢉꢅꢂꢐꢋꢆꢆ±ꢐꢋꢎꢏꢂPꢂꢈꢁ+ꢉꢋꢂ
ꢂ
ꢂ
ꢂ
ꢂ
DQGꢂ6KLEDVDNLꢅꢂ0ꢋꢅꢂ$QJHZ &KHPꢈꢀ ,QWꢈ (Gꢈ (QJOꢋꢅꢂꢆꢇꢇꢇꢅꢂ
YROꢋꢂꢍꢏꢅꢂSꢋꢂꢃꢄꢎꢇꢋꢂꢂ
ꢈ5ꢂ5ꢉꢀꢋꢀ0HWK\OꢀꢇꢀꢈꢆꢀSKHQ\OHWK\ODPLQRꢉEXWDQHꢀ
QLWULOHꢁ ꢈ9,Mꢉꢂ>ꢆꢇ@ꢋꢂ,5ꢂVSHFWUXPꢂꢈ&+ &O ꢉꢅꢂ ꢅꢂFP ꢑꢁ
ꢍꢍꢍꢆꢋꢄꢂꢈ1+ꢉꢅꢂꢆꢆꢎꢃꢋꢆꢂꢈ&1ꢉꢋꢂ +ꢂ105ꢂVSHFWUXPꢂꢂ
ꢈꢎꢇꢇꢂ0+]ꢅꢂ&'&O ꢉꢅꢂ ꢅꢂSSPꢑꢂꢃꢋꢍꢄꢂPꢂꢈꢄ+ꢉꢅꢂꢃꢋꢀꢄꢂGꢂꢈꢍ+ꢅꢂꢂ
-ꢂ ꢂꢄꢋꢄꢂ+]ꢉꢅꢂꢃꢋꢐꢃꢂPꢂꢈꢃ+ꢉꢅꢂꢆꢋꢃꢃꢂVꢂꢈꢃ+ꢉꢅꢂꢍꢋꢄꢂGꢂꢈꢃ+ꢅꢂ-ꢂ ꢂ
ꢄꢋꢀꢂ+]ꢉꢅꢂꢀꢋꢆꢆꢂTꢂꢈꢃ+ꢅꢂ-ꢂ ꢂꢄꢋꢄꢂ+]ꢉꢅꢂꢐꢋꢆꢃ±ꢐꢋꢀꢎꢂPꢂꢈꢎ+ꢉꢋꢂ
ꢃꢇꢋꢂ 7DNDPXUDꢅꢂ 0ꢋꢅꢂ +DPDVKLPDꢅꢂ<ꢋꢅꢂ 8VXGDꢅꢂ +ꢋꢅꢂ .DQDLꢅꢂ 0ꢋꢅꢂ
ꢂ
ꢂ
DQGꢂ6KLEDVDNLꢅꢂ0ꢋꢅꢂ&KHPꢈ 3KDUPꢈ %XOOꢋꢅꢂꢆꢇꢇꢇꢅꢂYROꢋꢂꢀꢁꢅꢂ
Sꢋꢂꢃꢎꢁꢄꢋꢂ
ꢃꢃꢋꢂ 6DLGLꢅꢂ 0ꢋ5ꢋꢂ DQGꢂ $]L]Lꢅꢂ 1ꢋꢅꢂ 7HWUDKHGURQꢇ $V\PPHWU\ꢅꢂ
ꢆꢇꢇꢆꢅꢂYROꢋꢂꢃꢍꢅꢂSꢋꢂꢆꢎꢆꢍꢋꢂꢂ
ꢃꢆꢋꢂ 6DLGLꢅꢂ 0ꢋ5ꢋꢂ DQGꢂ $]L]Lꢅꢂ 1ꢋꢅꢂ 7HWUDKHGURQꢇ $V\PPHWU\ꢅꢂ
ꢆꢇꢇꢍꢅꢂYROꢋꢂꢃꢀꢅꢂSꢋꢂꢍꢁꢏꢋꢂꢂ
ꢂ
ꢂ
ꢈ5ꢂ5ꢉꢀꢊꢀ3KHQ\OꢀꢇꢀꢈꢆꢀSKHQ\OHWK\ODPLQRꢉEXWDQHꢀ
QLWULOHꢁꢈ9,Nꢉꢂ>ꢃꢀ@ꢋꢂ,5ꢂVSHFWUXPꢂꢈ&+ &O ꢉꢅꢂ ꢅꢂFP ꢑꢂ
ꢍꢍꢍꢀꢋꢀꢂꢈ1+ꢉꢅꢂꢆꢆꢀꢏꢋꢃꢂꢈ&1ꢉꢋꢂ +ꢂ105ꢂVSHFWUXPꢂꢂ
ꢈꢎꢇꢇꢂ0+]ꢅꢂ&'&O ꢉꢅꢂ ꢅꢂSSPꢑꢂꢃꢋꢀꢁꢂGꢂꢈꢍ+ꢅꢂ-ꢂ ꢂꢄꢋꢎꢂ+]ꢉꢅꢂ
ꢃꢋꢁꢍꢂVꢂꢈꢃ+ꢉꢅꢂꢆꢋꢄꢆꢂPꢂꢈꢆ+ꢉꢅꢂꢍꢋꢆꢆꢂWꢂꢈꢆ+ꢅꢂ-ꢂ ꢂꢐꢋꢀꢂ+]ꢉꢅꢂꢂ
ꢍꢋꢐꢃꢂWꢂꢈꢃ+ꢅꢂ-ꢂ ꢂꢐꢋꢆꢂ+]ꢉꢅꢂꢀꢋꢍꢆꢂTꢂꢈꢃ+ꢅꢂ-ꢂ ꢂꢄꢋꢎꢂ+]ꢉꢅꢂꢐꢋꢆꢍ±
ꢐꢋꢎꢁꢂPꢂꢈꢃꢇ+ꢉꢋꢂ
ꢃꢍꢋꢂ 1DLPLꢊ-DPDOꢅꢂ0ꢋ5ꢋꢅꢂ,SDNWVFKLꢅꢂ-ꢋꢅꢂDQGꢂ6DLGLꢅꢂ0ꢋ5ꢋꢅꢂ(XUꢈ
-ꢈ 2UJꢈ &KHPꢋꢅꢂꢆꢇꢇꢇꢅꢂSꢋꢂꢃꢐꢍꢎꢋꢂ
ꢃꢀꢋꢂ 6WRXWꢅꢂ 'ꢋꢅꢂ %ODFNꢅꢂ / ꢋꢅꢂ DQGꢂ 0DWLHUꢅꢂ :ꢋꢅꢂ-ꢈ 2UJꢈ &KHPꢋꢅꢂ
ꢂ
ꢃꢏꢁꢍꢅꢂYROꢋꢂꢀꢁꢅꢂSꢋꢂꢎꢍꢄꢏꢋꢂꢂ
ꢃꢎꢋꢂ +\GDULꢅꢂ$ꢋꢅꢂ)DWHPLꢅꢂ3ꢋꢅꢂDQGꢂ$OL]DGHKꢅꢂ$ꢋ$ꢋꢅꢂ7HWUDKHGURQ
/HWWꢋꢅꢂꢃꢏꢏꢁꢅꢂYROꢋꢂꢍꢏꢅꢂSꢋꢂꢍꢇꢀꢏꢋꢂ
ꢃꢄꢋꢂ / HFOHUFꢅꢂ (ꢋꢅꢂ 0DQJHQH\ꢅꢂ 3ꢋꢅꢂ DQGꢂ +HQU\RQꢅꢂ 9ꢋꢅꢂ7HWUDꢅ
KHGURQꢇ $V\PPHWU\ꢅꢂꢆꢇꢇꢇꢅꢂYROꢋꢂꢃꢃꢅꢂSꢋꢂꢍꢀꢐꢃꢋꢂ
7KHꢂDXWKRUVꢂDUHꢂJUDWHIXOꢂWRꢂWKHꢂ5HVHDUFKꢂ&RXQFLOꢂRIꢂ
6KDULIꢂ8QLYHUVLW\ꢂRIꢂ7HFKQRORJ\ꢂIRUꢂILQDQFLDOꢂVXSSRUWꢋꢂ
:HꢂDOVRꢂWKDQNꢂ9RONVZDJHQꢊ6WLIWXQJꢂꢈ)HGHUDOꢂ5HSXEOLFꢂ
RIꢂ*HUPDQ\ꢉꢂIRUꢂILQDQFLDOꢂVXSSRUWꢂWRZDUGꢂSXUFKDVHꢂRIꢂ
HTXLSPHQWVꢂDQGꢂFKHPLFDOVꢋꢂ
ꢃꢐꢋꢂ <DGDYꢅꢂ -ꢋ6ꢋꢅꢂ 5HGG\ꢅꢂ %ꢋ9ꢋ6ꢋꢅꢂ (VKZDUDLDKꢅꢂ %ꢋꢅꢂ DQGꢂ
ꢂ
6ULQLYDVꢅꢂ0ꢋꢅꢂ1HZꢈ -ꢈ &KHPꢋꢅꢂꢆꢇꢇꢍꢅꢂYROꢋꢂꢆꢐꢅꢂSꢋꢂꢀꢄꢆꢋꢂ
ꢃꢁꢋꢂ /RYHOꢅꢂ ,ꢋꢅꢂ *RORPEDꢅꢂ /ꢋꢅꢂ %HO\DNRYꢅꢂ 6ꢋꢅꢂ 3RSHOLVꢅꢂ -ꢋꢅꢂ
ꢂ
*ULQEHUJDꢅꢂ 6ꢋꢅꢂ DQGꢂ /HXNHYLVꢅꢂ (ꢋꢅꢂ $SSOꢈ 2UJDQRPHWꢈ
&KHPꢋꢅꢂꢆꢇꢇꢇꢅꢂYROꢋꢂꢃꢀꢅꢂSꢋꢂꢐꢆꢃꢋꢂ
ꢃꢏꢋꢂ 6XQꢅꢂ 3ꢋꢅꢂ 4XLQꢅꢂ &ꢋꢅꢂ :DQJꢅꢂ /ꢋꢅꢂ DQGꢂ &KHQꢅꢂ 5ꢋꢅꢂ 6\QWKꢈ
&RPPXQꢋꢅꢂꢆꢇꢇꢆꢅꢂYROꢋꢂꢍꢆꢅꢂSꢋꢂꢆꢏꢐꢍꢋꢂ
5()(5(1&(6ꢂ
ꢂꢂꢃꢋꢂ 0DQVDZDWꢅꢂ :ꢋꢅꢂ %KDQWKXPQDYLQꢅꢂ :ꢋꢅꢂ DQGꢂ 9LODLYDQꢅꢂ 7ꢋꢅꢂ
ꢆꢇꢋꢂ ,QDKDꢅꢂ 7ꢋꢅꢂ )XMLWDꢅꢂ 0ꢋꢅꢂ DQGꢂ 2JXUDꢅꢂ .ꢋꢅꢂ -ꢈ 2UJꢈ &KHPꢋꢅꢂ
ꢂ
7HWUDKHGURQ /HWWꢋꢅꢂꢆꢇꢇꢍꢅꢂYROꢋꢂꢀꢀꢅꢂSꢋꢂꢍꢁꢇꢎꢋꢂ
ꢂ
ꢃꢏꢏꢃꢅꢂYROꢋꢂꢎꢄꢅꢂSꢋꢂꢃꢆꢀꢐꢋꢂ
5866,$1ꢂꢂ-2851$/ꢂꢂ2)ꢂꢂ25*$1,&ꢂꢂ&+(0,675<ꢂꢂꢂ9ROꢋꢂꢂꢀꢆꢂꢂꢂ1Rꢋꢂꢂꢃꢂꢂꢂꢆꢇꢇꢄꢂ