e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

One??Pot Synthesis of α??Amino Acids from Imines through CO2 Incorporation: An Alternative Method for Strecker Synthesis

T Mita, J Chen, M Sugawara…

Index: Mita, Tsuyoshi; Chen, Jianyang; Sugawara, Masumi; Sato, Yoshihiro Angewandte Chemie - International Edition, 2011 , vol. 50, # 6 p. 1393 - 1396

Full Text: HTML

Citation Number: 48

Abstract

Carbon dioxide is an abundant and inexpensive carbon source (C1 unit); however, its inertness and gaseous character sometimes hamper its use for efficient CÀC bond-forming reactions in organic synthesis. To overcome this problem, strongly nucleophilic organometallic regents, such as RLi and RMgX, are often used for CÀC bond construction that incorporates CO2.[1] Recently, transition-metal-promoted CO2 fixation reactions, ...

diazomethane Structure

N/A Structure

Carbon dioxide Structure

~14%

N/A Structure

Detail

N/A Structure

Carbon dioxide Structure

~%

2-((tert-Butoxycarbonyl)amino)-2-(naphthalen-2-yl)acetic acid Structure

2-((tert-Butoxy...

tert-butyl N-(naphthalen-2-ylmethyl)carbamate Structure

tert-butyl N-(n...

tert-Butyl carbamate Structure

tert-Butyl carbamate

~%

N/A Structure

tert-butyl N-(naphthalen-2-ylmethyl)carbamate Structure

tert-butyl N-(n...

tert-Butyl carbamate Structure

tert-Butyl carbamate

~%

2-((tert-Butoxycarbonyl)amino)-2-(naphthalen-2-yl)acetic acid Structure

2-((tert-Butoxy...

tert-butyl N-(naphthalen-2-ylmethyl)carbamate Structure

tert-butyl N-(n...

2-Naphthaldehyde Structure

2-Naphthaldehyde

~%

N/A Structure

tert-butyl N-(naphthalen-2-ylmethyl)carbamate Structure

tert-butyl N-(n...

2-Naphthaldehyde Structure

2-Naphthaldehyde

~%

2-((tert-Butoxycarbonyl)amino)-2-(naphthalen-2-yl)acetic acid Structure

2-((tert-Butoxy...

tert-butyl N-(naphthalen-2-ylmethyl)carbamate Structure

tert-butyl N-(n...

Benzaldehyde Structure

~%

tert-Butyl (phenylMethylene)carbaMate Structure

tert-Butyl (phe...

diazomethane Structure

Carbon dioxide Structure

2-Methyl-2-propanyl [(4-chlorophenyl)(phenylsulfonyl)methyl]carba mate Structure

2-Methyl-2-prop...

~65%

tert-butyl (Methoxycarbonyl)(4-chlorophenyl)Methylcarbamate Structure

tert-butyl (Met...

Detail

Carbon dioxide Structure

N/A Structure

~%

2-((TERT-BUTOXYCARBONYL)(3-FLUOROPHENYL)AMINO)ACETIC ACID Structure

2-((TERT-BUTOXY...

tert-Butyl 3-fluorobenzylcarbamate Structure

tert-Butyl 3-fl...

tert-Butyl carbamate Structure

tert-Butyl carbamate

~%

2-((TERT-BUTOXYCARBONYL)(3-FLUOROPHENYL)AMINO)ACETIC ACID Structure

2-((TERT-BUTOXY...

tert-Butyl 3-fluorobenzylcarbamate Structure

tert-Butyl 3-fl...

3-Fluorobenzaldehyde Structure

3-Fluorobenzaldehyde

~%

2-((TERT-BUTOXYCARBONYL)(3-FLUOROPHENYL)AMINO)ACETIC ACID Structure

2-((TERT-BUTOXY...

tert-Butyl 3-fluorobenzylcarbamate Structure

tert-Butyl 3-fl...

tert-Butyl carbamate Structure

tert-Butyl carbamate

~%

2-(4-fluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Structure

2-(4-fluorophen...

tert-Butyl (4-fluorobenzyl)carbamate Structure

tert-Butyl (4-f...

4-Fluorobenzaldehyde Structure

4-Fluorobenzaldehyde

~%

2-(4-fluorophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Structure

2-(4-fluorophen...

tert-Butyl (4-fluorobenzyl)carbamate Structure

tert-Butyl (4-f...

N/A Structure

Carbon dioxide Structure

~%

2-((tert-Butoxycarbonyl)amino)-2-(naphthalen-2-yl)acetic acid Structure

2-((tert-Butoxy...

tert-butyl N-(naphthalen-2-ylmethyl)carbamate Structure

tert-butyl N-(n...

tert-Butyl carbamate Structure

tert-Butyl carbamate

~%

2-((tert-Butoxycarbonyl)amino)-2-(naphthalen-2-yl)acetic acid Structure

2-((tert-Butoxy...

tert-butyl N-(naphthalen-2-ylmethyl)carbamate Structure

tert-butyl N-(n...

2-Naphthaldehyde Structure

2-Naphthaldehyde

~%

2-((tert-Butoxycarbonyl)amino)-2-(naphthalen-2-yl)acetic acid Structure

2-((tert-Butoxy...

tert-butyl N-(naphthalen-2-ylmethyl)carbamate Structure

tert-butyl N-(n...

Carbon dioxide Structure

N/A Structure

~%

2-((tert-Butoxycarbonyl)amino)-2-(p-tolyl)acetic acid Structure

2-((tert-Butoxy...

tert-Butyl 4-methylbenzylcarbamate Structure

tert-Butyl 4-me...

tert-Butyl carbamate Structure

tert-Butyl carbamate

~%

2-((tert-Butoxycarbonyl)amino)-2-(p-tolyl)acetic acid Structure

2-((tert-Butoxy...

tert-Butyl 4-methylbenzylcarbamate Structure

tert-Butyl 4-me...

p-Tolualdehyde Structure

~%

2-((tert-Butoxycarbonyl)amino)-2-(p-tolyl)acetic acid Structure

2-((tert-Butoxy...

tert-Butyl 4-methylbenzylcarbamate Structure

tert-Butyl 4-me...

tert-butyl N-[benzenesulfonyl(phenyl)methyl]carbamate Structure

tert-butyl N-[b...

~9%

N-Boc benzylamine Structure

N-Boc benzylamine

Benzaldehyde Structure

~%

N-Boc benzylamine Structure

N-Boc benzylamine

Carbon dioxide Structure

tert-butyl N-[benzenesulfonyl(phenyl)methyl]carbamate Structure

tert-butyl N-[b...

~%

N-Boc benzylamine Structure

N-Boc benzylamine

BOC-D-PHG-OH Structure

diazomethane Structure

Carbon dioxide Structure

tert-Butyl (phenylMethylene)carbaMate Structure

tert-Butyl (phe...

~36%

N-Boc benzylamine Structure

N-Boc benzylamine

Detail

Chemoselective conversion of azides to t-butyl carbamates an...

[Jung, Yeon Joo; Chang, Yu Mi; Lee, Ji Hee; Yoon, Cheol Min Tetrahedron Letters, 2002 , vol. 43, # 48 p. 8735 - 8739]

Synthesis and Application of a New Fluorous??Tagged Ammonia ...

[Nielsen, Simon D.; Smith, Garrick; Begtrup, Mikael; Kristensen, Jesper L. Chemistry - A European Journal, 2010 , vol. 16, # 15 p. 4557 - 4566]

Improved synthesis of (R)-glycine-d-15 N

[Walker, Joel R; Curley Jr., Robert W Tetrahedron, 2001 , vol. 57, # 31 p. 6695 - 6701]

Improved synthesis of (R)-glycine-d-15 N

[Walker, Joel R; Curley Jr., Robert W Tetrahedron, 2001 , vol. 57, # 31 p. 6695 - 6701]

Improved synthesis of (R)-glycine-d-15 N

[Walker, Joel R; Curley Jr., Robert W Tetrahedron, 2001 , vol. 57, # 31 p. 6695 - 6701]