scholarly journals Regioselective SN2' Mitsunobu reaction of Morita–Baylis–Hillman alcohols: A facile and stereoselective synthesis of α-alkylidene-β-hydrazino acid derivatives

2014 ◽  
Vol 10 ◽  
pp. 990-995 ◽  
Author(s):  
Silong Xu ◽  
Jian Shang ◽  
Junjie Zhang ◽  
Yuhai Tang
Keyword(s):  
Stereoselective Synthesis ◽  
Mitsunobu Reaction ◽  
Easy Access ◽  
Direct Transformation ◽  
High Yields

A highly regioselective SN2' Mitsunobu reaction between Morita–Baylis–Hillman (MBH) alcohols, azodicarboxylates, and triphenylphosphine is developed, which provides an easy access to α-alkylidene-β-hydrazino acid derivatives in high yields and good stereoselectivity. This reaction represents the first direct transformation of MBH alcohols into hydrazines.

ChemInform Abstract: L-Proline Catalyzed Stereoselective Synthesis of (E)-Methyl-α-indol-2-yl-β-aryl/alkyl Acrylates: Easy Access to Substituted Carbazoles, γ-Carbolines and Prenostodione.

ChemInform ◽  
2014 ◽  
Vol 45 (9) ◽  
pp. no-no
Author(s):  
Soumen Biswas ◽  
Pradeep Kumar Jaiswal ◽  
Shivendra Singh ◽  
Shaikh M. Mobin ◽  
Sampak Samanta
Keyword(s):  
Stereoselective Synthesis ◽  
Easy Access ◽  
Alkyl Acrylates

l-Proline catalyzed stereoselective synthesis of (E)-methyl-α-indol-2-yl-β-aryl/alkyl acrylates: easy access to substituted carbazoles, γ-carbolines and prenostodione

2013 ◽  
Vol 11 (41) ◽  
pp. 7084 ◽  
Author(s):  
Soumen Biswas ◽  
Pradeep Kumar Jaiswal ◽  
Shivendra Singh ◽  
Shaikh M. Mobin ◽  
Sampak Samanta
Keyword(s):  
Stereoselective Synthesis ◽  
Easy Access ◽  
Alkyl Acrylates

scholarly journals Unconventional application of the Mitsunobu reaction: Selective flavonolignan dehydration yielding hydnocarpins

2016 ◽  
Vol 12 ◽  
pp. 662-669 ◽  
Author(s):  
Guozheng Huang ◽  
Simon Schramm ◽  
Jörg Heilmann ◽  
David Biedermann ◽  
Vladimír Křen ◽  
...  
Keyword(s):  
Mitsunobu Reaction ◽  
Synthetic Method ◽  
One Pot ◽  
Selective Esterification ◽  
C 23 ◽  
High Yields

Various Mitsunobu conditions were investigated for a series of flavonolignans (silybin A, silybin B, isosilybin A, and silychristin A) to achieve either selective esterification in position C-23 or dehydration in a one-pot reaction yielding the biologically important enantiomers of hydnocarpin D, hydnocarpin and isohydnocarpin, respectively. This represents the only one-pot semi-synthetic method to access these flavonolignans in high yields.

Formation of heterocycles by the Mitsunobu reaction. Stereoselective synthesis of (+)-α-skytanthine

1996 ◽  
Vol 37 (14) ◽  
pp. 2463-2466 ◽  
Author(s):  
Tetsuto Tsunoda ◽  
Fumie Ozaki ◽  
Nozomi Shirakata ◽  
Yuki Tamaoka ◽  
Hidetoshi Yamamoto ◽  
...  
Keyword(s):  
Stereoselective Synthesis ◽  
Mitsunobu Reaction

A Stereoselective Synthesis of (E)-Allylic Alcohols Via the Hydromagnesiation of Alkynylsilanes

2003 ◽  
Vol 2003 (5) ◽  
pp. 296-298 ◽  
Author(s):  
Mingzhong Cai ◽  
Chunyun Peng ◽  
Hong Zhao ◽  
Wenyan Hao
Keyword(s):  
Stereoselective Synthesis ◽  
Grignard Reagents ◽  
Allylic Alcohols ◽  
High Yields

Hydromagnesiation of alkynylsilanes 1 gives ( Z)-α-silylvinyl Grignard reagents 2, which are reacted with aldehydes or ketones to afford ( Z)-β-silyl allylic alcohols 3 in high yields; intermediates 3 can undergo the desilylation reaction in the presence of anhydrous KF to give ( E)-allylic alcohols 4 in good yields.

Carbamoyl anion-initiated cascade reaction for stereoselective synthesis of substituted α-hydroxy-β-amino amides

2016 ◽  
Vol 52 (5) ◽  
pp. 912-915 ◽  
Author(s):  
Chao-Yang Lin ◽  
Peng-Ju Ma ◽  
Zhao Sun ◽  
Chong-Dao Lu ◽  
Yan-Jun Xu
Keyword(s):  
Stereoselective Synthesis ◽  
Cascade Reaction ◽  
Rapid Construction ◽  
High Yields ◽  
Amino Amides

A carbamoyl anion-initiated cascade reaction with acylsilanes and imines allows rapid construction of substituted α-hydroxy-β-amino amides in high yields with excellent diastereoselectivities.

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