Synthesis of β-hydroxy-δ-trichloromethyl-δ-valerolactones by intramolecular samarium/ytterbium diiodide-mediated Reformatsky reaction

被引：2

作者：

Schulze, Thies M. ^{[1
]}

Grunenberg, Joerg ^{[1
]}

Schulz, Stefan ^{[1
]}

机构：

[1] Tech Univ Carolo Wilhelmina Braunschweig, Inst Organ Chem, D-38106 Braunschweig, Germany

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 08期

关键词：

Lactones; Intramolecular Reformatsky reaction; Samarium diiodide; Ytterbium diiodide; Trichloromethyl group; Kinetic resolution; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; EFFICIENT; BIOSYNTHESIS; LACTONES;

D O I：

10.1016/j.tetlet.2012.11.146

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of alpha-methyl-beta-hydroxy-delta-trichloromethyl-delta-valerolactone was achieved by an intramolecular Reformatsky reaction. The cyclisation was effected by samarium diiodide or (for the first time) ytterbium diiodide. The diastereoselectivity of the reaction corresponds to earlier investigations by Molander. Consecutive stereoselective reactions during the esterification to the Reformatsky precursor 1,1,1-trichloropent-4-en-2-yl 2-bromopropanoate and in the Reformatslcy reaction itself led to (3RS,4RS,6SR)-4-hydroxy-3-methyl-6-(trichloromethyl)tetrahydro-2H-pyran-2-one (3a) as the major formed diastereomer. The influence of the orientation of the substituents in the transition state is discussed. (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：921 / 924

页数：4

共 45 条

[1] TRIHALOGENOMETHYL COMPOUNDS OF POTENTIAL THERAPEUTIC INTEREST .6. SOME ALCOHOLS WITH SEDATIVE ACTION AND THEIR ESTERS
BISHOP, DC
MEACOCK, SCR
WILLIAMSON, WR
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1966, (07): : 670 - +
[2] Reeve's synthesis of 2-imino-4-thiazolidinone from alkyl (aryl) trichloromethylcarbinol revisited, a three-component process from aldehyde, chloroform and thiourea
Blanchet, J
Zhu, JP
[J]. TETRAHEDRON LETTERS, 2004, 45 (23) : 4449 - 4452
[3] Lipase enhanced catalytic efficiency in lactonisation reactions
Bonini, C
Cazzato, C
Cernia, E
Palocci, C
Soro, S
Viggiani, L
[J]. JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2001, 16 (01) : 1 - 5
[4] Synthesis and structures of Ln(II) and Ln(III) dialkyls derived from LnI2 (Ln = Nd, Tm, Yb)
Bowman, Lyndsey J.
Izod, Keith
Clegg, William
Harrington, Ross W.
[J]. ORGANOMETALLICS, 2007, 26 (10) : 2646 - 2651
[5] (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone as chiral auxiliaries for the asymmetric synthesis of alpha-hydroxy acids
Camps, P
Perez, F
Soldevilla, N
[J]. TETRAHEDRON-ASYMMETRY, 1997, 8 (11) : 1877 - 1894
[6] SOLID ANGLE AS STERIC PARAMETER OF ACYCLIC SATURATED GROUPS
CHAUVIN, R
KAGAN, HB
[J]. CHIRALITY, 1991, 3 (04) : 242 - 253
[7] A catalytic, Me2Zn-mediated, enantioselective reformatsky reaction with ketones
Cozzi, Pier Giorgio
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (18) : 2951 - 2954
[8] TCP- and phthalimide-protected n-pentenyl glucosaminide precursors for the synthesis of nodulation factors as illustrated by the total synthesis of NodRf-III (C18:1, MeFuc)
Debenham, JS
Rodebaugh, R
FraserReid, B
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (14) : 4591 - 4600
[9] ASYMMETRIC-SYNTHESIS OF ALPHA-HALO ESTERS
DURST, T
KOH, K
[J]. TETRAHEDRON LETTERS, 1992, 33 (45) : 6799 - 6802
[10] Samarium(II)-iodide-mediated cyclizations in natural product synthesis
Edmonds, DJ
Johnston, D
Procter, DJ
[J]. CHEMICAL REVIEWS, 2004, 104 (07) : 3371 - 3403

← 1 2 3 4 5 →