Role of the countercation in diastereoselective alkylations of pyramidalized bicyclic serine enolates.: An easy approach to α-benzylserine

被引：27

作者：

Jimenez-Oses, Gonzalo ^{[1
]}

Aydillo, Carlos ^{[1
]}

Busto, Jesus H. ^{[1
]}

Zurbano, Maria M. ^{[1
]}

Peregrina, Jesus M. ^{[1
]}

Avenoza, Alberto ^{[1
]}

机构：

[1] Univ La Rioja, Dept Quim, Grp Sintesis Quim La Rioja, UA CSIC, Logrono 26006, Spain

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 14期

关键词：

D O I：

10.1021/jo070656b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of a chiral serine equivalent as an excellent chiral building block has been demonstrated in the synthesis of alpha-benzylserine through a diastereoselective lithium enolate alkylation reaction and subsequent acid hydrolysis. The role of a coordinating countercation (lithium) in the alkylation reaction has been investigated. Theoretical studies have been performed in order to elucidate the stereochemical outcome of the alkylation process, which occurs with total retention of configuration.

引用

页码：5399 / 5402

页数：4

共 46 条

[1] Ab initio and semiempirical study of the effect of ethereal solvent on aggregation of a lithium enolate [J].

Abbotto, A ;

Streitwieser, A ;

Schleyer, PV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (46) :11255-11268

[2] The role of monomer in alkylation reactions of the lithium enolate of p-phenylisobutyrophenone in tetrahydrofuran [J].

Abbotto, A ;

Leung, SSW ;

Streitwieser, A ;

Kilway, KV .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (42) :10807-10813

[3] ASYMMETRIC ALKYLATION OF 8-PHENYLMENTHYL N-[BIS(METHYLTHIO)METHYLENE]GLYCINATE ENOLATES - SYNTHESIS OF D-ALPHA-AMINO AND L-ALPHA-AMINO ACIDS FROM A SINGLE CHIRAL PRECURSOR [J].

ALVAREZIBARRA, C ;

CSAKY, AG ;

MAROTO, R ;

QUIROGA, ML .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (24) :7934-7940

[4] Diastereoselective synthesis of (S)- and (R)-α-phenylserine by a sulfinimine-mediated Strecker reaction [J].

Avenoza, A ;

Busto, JH ;

Corzana, F ;

Peregrina, JM ;

Sucunza, D ;

Zurbano, MM .

SYNTHESIS-STUTTGART, 2005, (04) :575-578

[5] α-Methylserinals as an access to α-methyl-β-hydroxyamino acids:: application in the synthesis of all stereoisomers of α-methylthreonine [J].

Avenoza, A ;

Busto, JH ;

Corzana, F ;

Peregrina, JM ;

Sucunza, D ;

Zurbano, MM .

TETRAHEDRON-ASYMMETRY, 2004, 15 (04) :719-724

[6] Synthesis of enantiopure (αMe)Dip and other α-methylated β-branched amino acid derivatives [J].

Avenoza, A ;

Busto, JH ;

Cativiela, C ;

Peregrina, JM ;

Sucunza, D ;

Zurbano, MM .

TETRAHEDRON-ASYMMETRY, 2003, 14 (03) :399-405

[7] Enantioselective synthesis of (S)- and (R)-α-methylserines:: application to the synthesis of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals [J].

Avenoza, A ;

Cativiela, C ;

Corzana, F ;

Peregrina, JM ;

Sucunza, D ;

Zurbano, MM .

TETRAHEDRON-ASYMMETRY, 2001, 12 (06) :949-957

[8] Asymmetric synthesis of all isomers of α-methyl-β-phenylserine [J].

Avenoza, A ;

Cativiela, C ;

Corzana, F ;

Peregrina, JM ;

Zurbano, MM .

TETRAHEDRON-ASYMMETRY, 2000, 11 (10) :2195-2204

[9] A straightforward synthesis of both enantiomers of α-vinylalanine and α-ethynylalanine [J].

Avenoza, A ;

Cativiela, C ;

Peregrina, JM ;

Sucunza, D ;

Zurbano, MM .

TETRAHEDRON-ASYMMETRY, 1999, 10 (23) :4653-4661

[10] Preparation and synthetic applications of (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals:: Asymmetric synthesis of (S)- and (R)-2-amino-2-methylbutanoic acids (Iva) [J].

Avenoza, A ;

Cativiela, C ;

Corzana, F ;

Peregrina, JM ;

Zurbano, MM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8220-8225

← 1 2 3 4 5 →